[ CAS No. 42882-31-5 ] {[proInfo.proName]}

Name: 42882-31-5|1-(Naphthalen-1-yl)ethanamine|98%
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SKU: A113145
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Quality Control of [ 42882-31-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 42882-31-5 ]

Product Details of [ 42882-31-5 ]

CAS No. :	42882-31-5	MDL No. :	MFCD00004014
Formula :	C₁₂H₁₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RTCUCQWIICFPOD-UHFFFAOYSA-N
M.W :	171.24	Pubchem ID :	98089
Synonyms :

Calculated chemistry of [ 42882-31-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.43
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	2.76
Log Po/w (WLOGP) :	2.54
Log Po/w (MLOGP) :	2.85
Log Po/w (SILICOS-IT) :	2.77
Consensus Log Po/w :	2.59

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.14
Solubility :	0.123 mg/ml ; 0.000718 mol/l
Class :	Soluble
Log S (Ali) :	-2.96
Solubility :	0.187 mg/ml ; 0.00109 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.14
Solubility :	0.0123 mg/ml ; 0.0000718 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.12

Safety of [ 42882-31-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 42882-31-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 42882-31-5 ]
Downstream synthetic route of [ 42882-31-5 ]

[ 42882-31-5 ] Synthesis Path-Upstream 1~9

1
[ 941-98-0 ]
[ 42882-31-5 ]

Yield	Reaction Conditions	Operation in experiment
40%	With hydroxylamine hydrochloride; ammonium formate; zinc In methanol for 5 h; Reflux	The corresponding ketone (10 mmol: 1.14 g of 1a, 0.98 g of 1b, 1.48 g of 1c, 1.46 g of1d, 1.46 g of 1e, 1.32 g of 1f, 1.20 g of 1g, 1.70 g of 1h, 1.70 g of 1i), hydroxylamine hydrochloride (15mmol, 1.04 g), ammonium formate (60 mmol, 3.78 g) and Zn powder (30 mmol, 1.96 g) in methanol (30mL) was stirred under reflux. After completion of the reaction the mixture was filtered through Celite.(R). andthe solvent was removed by vacuum rotary evaporation. The residue was treated with conc. HCl solution (4mL) and water (30 mL), and then extracted with diethyl ether (2x20 mL) to remove organic residues. Theaqueous phase was alkalized with ammonia solution to pH=10 and extracted with dichloromethane (4x25mL). The organic phase was washed with brine, dried over sodium sulfate and the solvent removed undervacuum.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1310 - 1312
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6197 - 6208
[3] Patent: WO2008/58235, 2008, A2, . Location in patent: Page/Page column 23-24
[4] Synthetic Communications, 2011, vol. 41, # 3, p. 341 - 346
[5] Molecules, 2014, vol. 19, # 12, p. 21386 - 21397
[6] European Journal of Organic Chemistry, 2015, vol. 2015, # 24, p. 5393 - 5401

2
[ 344248-49-3 ]
[ 42882-31-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride In ethanol at 20℃; for 2 h;	Gaseous hydrogen chloride was bubbled through a stirred solution of N-diphenylphosphinyl-1-naphthylethylamine in ethyl alcohol for 2 hours at room temperature. The reaction mixture was concentrated, made basic by the addition of an aqueous solution of sodium hydroxide (2 M) and extracted with dichloromethane (3.x.10 ml). The organic layer was washed with brine (1.x.10 ml), dried over magnesium sulphate and concentrated to give the product as a yellow liquid in 80percent yield.

Reference： [1] Patent: US6696608, 2004, B1, . Location in patent: Page column 28

3
[ 1956-40-7 ]
[ 42882-31-5 ]

Reference： [1] Synthetic Communications, 2011, vol. 41, # 3, p. 341 - 346
[2] Tetrahedron, 1994, vol. 50, # 34, p. 10309 - 10320

4
[ 10420-89-0 ]
[ 946113-79-7 ]
[ 42882-31-5 ]

Reference： [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 1, p. 113 - 121

5
[ 3886-70-2 ]
[ 42882-31-5 ]

Reference： [1] Patent: US2013/345475, 2013, A1, . Location in patent: Paragraph 0117

6
[ 3886-70-2 ]
[ 1127-76-0 ]
[ 42882-31-5 ]

Reference： [1] Patent: US2013/345475, 2013, A1, . Location in patent: Paragraph 0116

7
[ 49681-33-6 ]
[ 42882-31-5 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 6, p. 1469 - 1472

8
[ 75-31-0 ]
[ 42882-31-5 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 16, p. 3804 - 3809

9
[ 42882-31-5 ]
[ 178306-51-9 ]
[ 178306-52-0 ]

Reference： [1] Patent: US2014/256004, 2014, A1, . Location in patent: Page/Page column

[ 42882-31-5 ] Synthesis Path-Downstream 1~88

1
[ 42882-31-5 ]
[ 3886-70-2 ]

Yield	Reaction Conditions	Operation in experiment
88.3%	With p-chlorophenyl pentanoate; hydrogen; In toluene; at 55℃; under 75.0075 Torr; for 15h;Enzymatic reaction;	In a 250 mL three-necked flask, mechanical stirring was slow,Toluene, 4 g of racemic naphthylethylamine, 5.2 g of acyl donor p-chlorophenol valerate, 1 g of Pd / LDH-SA and 0.4 g of lipaseNovozym 435, hydrogen pressure of 0.01MPa, 55 C under the conditions of reaction 15h, gas chromatography, Naphthylamine reaction completely, The catalyst (lipase and racemic catalyst) was removed by filtration and used in the next reaction, and the toluene solution was dissolved with sodium hydroxide(R) -amide; and the resulting (R) -amide was stirred at room temperature for 2 hours to remove p-chlorophenol, then dried and evaporated to dryness under reduced pressure to give2mol / L dilute hydrochloric acid hydrolysis 80 C 10h, then add ammonia to adjust pH> 10,0.5h after the dichloromethane burning extraction, drying, rotary steamTo give 3.538 (10-1- (1-naphthyl) ethylamine in a yield of 88.3%.

Reference： [1]Patent: CN104592037,2016,B .Location in patent: Paragraph 0040
[2]Diss.<Lund 1923>S.51,
[3]Synthetic Communications,2011,vol. 41,p. 341 - 346
[4]Patent: WO2014/178068,2014,A2

2
[ 371-27-7 ]
[ 42882-31-5 ]
[ 3886-70-2 ]
[ 87782-88-5 ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 3094 - 3095
[2]Journal of Organic Chemistry,1997,vol. 62,p. 3488 - 3495

3
[ 1956-40-7 ]
[ 42882-31-5 ]

Reference： [1]Synthetic Communications,2011,vol. 41,p. 341 - 346
[2]Tetrahedron,1994,vol. 50,p. 10309 - 10320

4
[ 42882-31-5 ]
[ 941-98-0 ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 4986 - 4990
[2]Synthetic Communications,1989,vol. 19,p. 3407 - 3412
[3]Canadian Journal of Chemistry,2012,vol. 90,p. 39 - 45
[4]Organic Letters,2015,vol. 17,p. 1469 - 1472

5
[ 42882-31-5 ]
[ 10420-89-0 ]
[ 3886-70-2 ]

Yield	Reaction Conditions	Operation in experiment
	With chiral stationary phase including isopropyl-functionalized CF6; In methanol; acetic acid; triethylamine; acetonitrile; at 20℃;Purification / work up;	In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.\|0132\| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.\|0133\| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.\|0134\| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.\|0135\| For the calculations of chromatographic data, the "dead time" to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode.
82.9 g; 81.32 g		2.5 L isopropanol was added 171.2 g (1 mol) of 1-naphthylethylamine and 237.4 g (0.98 mol)(+) - 4-phenyl-2-light-5,5-ene-methyl-2-oxo-1,3,2-oxy ether, 5.53 g (0.02 mol)(+) - 4- (2-chlorophenyl) -2-hydroxy-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorane, heated to refluxClarification, stirring lh, cooling crystallization, filtration, washing with 200mL isopropanol filter cake, get 202.4g white solid, namely (R) -l-1_naphthalene ethylamine complex salt. The above filter cake was dissolved in 500 mL of water,With 10% K0H solution adjusted rhoH- = 8,Stirring at room temperature lh,Extracted three times with methylene chloride,Each time the amount of 100mL,Drying the organic layer,(R) - (+) - l-naphthylethylamine (81.32 g) Yield 95%99.2% e.Solid optically active f: + 47.2 (c = l methanol) was measured.Water layer with hydrochloric acid to adjust the pH to strong acid,Stirring a large amount of solid at room temperature,Filter, recovery split agent. The filtrate and the washing liquid in step a are combined,The organic solvent was distilled off,The resulting solid was dissolved in 500 mL of water,With 10% Na0H solution adjusted rhoH- = 8,Stirring at room temperature lh,Extracted three times with methylene chloride,Each time the amount of 100mL,Drying the organic layer,The organic solvent was distilled off,To obtain -(i) -naphthalene ethylamine 82.9g,The yield was 96.8%96.3% e.Water layer transferred to strong acidity,Stir at room temperature, suction filtration, recovery of the remaining resolving agent

Reference： [1]Tetrahedron Asymmetry,2002,vol. 13,p. 2277 - 2282
[2]Tetrahedron,1994,vol. 50,p. 10309 - 10320
[3]Tetrahedron Asymmetry,1994,vol. 5,p. 817 - 820
[4]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 1339 - 1347
[5]Journal of the Chinese Chemical Society,2009,vol. 56,p. 1163 - 1167
[6]Patent: WO2010/148191,2010,A2 .Location in patent: Page/Page column 45-49; 61
[7]Chemistry - An Asian Journal,2016,vol. 11,p. 3513 - 3519
[8]Patent: CN104829459,2017,B .Location in patent: Paragraph 0040-0044; 0045-0049; 0050-0054; 0075-0078

6
[ 19542-34-8 ]
[ 42882-31-5 ]
{(S)-1-[(S)-2-Hydroxy-1-((S)-1-naphthalen-1-yl-ethylcarbamoyl)-ethylcarbamoyl]-ethyl}-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 5317 - 5320

7
[ 42882-31-5 ]
[ 103063-37-2 ]
N-[Z-(S)-Phe]-(S)-1-(1-naphthyl)ethylamine [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 5317 - 5320

8
[ 42882-31-5 ]
[ 4817-95-2 ]
{(S)-2-Methyl-1-[(S)-1-((S)-1-naphthalen-1-yl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-propyl}-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 5317 - 5320

9
[ 42882-31-5 ]
[ 4326-36-7 ]
[(S)-2-(4-Hydroxy-phenyl)-1-((S)-1-naphthalen-1-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 5317 - 5320

10
[ 42882-31-5 ]
2-tert-Butoxycarbonylamino-3-naphthalen-2-yl-propionic acid methyl ester [ No CAS ]
[(S)-2-Naphthalen-2-yl-1-((S)-1-naphthalen-1-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 5317 - 5320

11
[ 42882-31-5 ]
[ 176896-73-4 ]
[(S)-2-Naphthalen-2-yl-1-((S)-1-naphthalen-1-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 5317 - 5320

12
[ 19542-34-8 ]
[ 42882-31-5 ]
{(S)-1-[(S)-2-Hydroxy-1-(1-naphthalen-1-yl-ethylcarbamoyl)-ethylcarbamoyl]-ethyl}-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 3488 - 3495

13
[ 42882-31-5 ]
[ 4817-95-2 ]
{(S)-2-Methyl-1-[(S)-1-(1-naphthalen-1-yl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-propyl}-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 3488 - 3495

14
[ 42882-31-5 ]
2-tert-Butoxycarbonylamino-3-naphthalen-2-yl-propionic acid methyl ester [ No CAS ]
[(S)-2-Naphthalen-2-yl-1-(1-naphthalen-1-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 3488 - 3495

15
[ 42882-31-5 ]
[ 176896-73-4 ]
[(S)-2-Naphthalen-2-yl-1-(1-naphthalen-1-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 3488 - 3495

16
[ 13398-81-7 ]
[ 42882-31-5 ]
<i>N</i>,<i>N</i>'-bis-(1-naphthalen-1-yl-ethyl)-phenazine-1,6-diamine [ No CAS ]

Reference： [1]Chemical Communications,2004,p. 412 - 413

17
[ 13031-04-4 ]
[ 42882-31-5 ]
(+)-(1'S,2S)-N-[1'-(1-naphthyl)ethyl]-2-amino-3,3-dimethyl-γ-butyrolactone [ No CAS ]
(-)-(1'R,2R)-N-[1'-(1-naphthyl)ethyl]-2-amino-3,3-dimethyl-γ-butyrolactone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 78 - 86

18
[ 875148-76-8 ]
[ 42882-31-5 ]
4-oxo-1-pentyl-1,4-dihydro-quinoline-3-carboxylic acid (1-naphthalen-1-yl-ethyl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 70 - 79

19
(meso)-7-(4-nitrobenzenesulfonyl)-7-azabicyclo[4.1.0]heptane [ No CAS ]
[ 42882-31-5 ]
PHD 397 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5119 - 5128

20
[ 42882-31-5 ]
[ 115617-41-9 ]
(5-chloro-6-ethyl-pyrimidin-4-yl)-(1-naphthalen-1-yl-ethyl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 260 - 265

21
[ 941-98-0 ]
[ 42882-31-5 ]

Yield	Reaction Conditions	Operation in experiment
40%	With hydroxylamine hydrochloride; ammonium formate; zinc; In methanol; for 5h;Reflux;	The corresponding ketone (10 mmol: 1.14 g of 1a, 0.98 g of 1b, 1.48 g of 1c, 1.46 g of1d, 1.46 g of 1e, 1.32 g of 1f, 1.20 g of 1g, 1.70 g of 1h, 1.70 g of 1i), hydroxylamine hydrochloride (15mmol, 1.04 g), ammonium formate (60 mmol, 3.78 g) and Zn powder (30 mmol, 1.96 g) in methanol (30mL) was stirred under reflux. After completion of the reaction the mixture was filtered through Celite andthe solvent was removed by vacuum rotary evaporation. The residue was treated with conc. HCl solution (4mL) and water (30 mL), and then extracted with diethyl ether (2x20 mL) to remove organic residues. Theaqueous phase was alkalized with ammonia solution to pH=10 and extracted with dichloromethane (4x25mL). The organic phase was washed with brine, dried over sodium sulfate and the solvent removed undervacuum.
	With ammonium formate; at 165℃; for 8 - 10h;	EXAMPLE 3: PREPRATION OF RACEMIC 1-(1-NAPTHYL) ETHYLAMINE:1-acetonaphthone (200 g) and ammonium formate (370 g) were taken into a round bottom flask and Dean and stalk apparatus was arranged. The reaction mass was heated to about 165 C and maintained for about 8-10 hrs, the collected water was discarded. Reaction completion was checked using thin layer chromatography, and after the reaction was completed, the reaction mass was allowed to cool to about 50 C and HCI (200 ml) was added to it slowly, and stir for 10-15 min at 50 C. Add methanol (200 ml) slowly and then maintained for 15- 20 min.The reaction mass was filtered through a hyflow bed and the bed was washed with methanol (400 ml). The filtrate was taken into another round bottom and add HCI (400 ml) slowly at 25-35C, and the contents were heated to about 65 C. The reaction mass was maintained at about 65 C for about 3-4 hours and then cooled to about 25-35C. Water (1000 ml) was added to it under stirring EPO <DP n="25"/>followed by addition of dichloromethane (1000 ml). The reaction mass was stirred for about 10 minutes, and then the organic layer was separated. The aqueous layer was washed with dichloromethane (1000 ml). The combined DCM washing layers were extracted with DM-Water (1000 ml). The combined aq. layer pH was then adjusted to about 10-12 using caustic lye and then extracted into dichloromethane (2000 ml) in two lots. The combined organic layer was washed with 2000 ml of water in two lots. The organic layer was distilled off completely under a vacuum of about 650 mm/Hg at 48C to yield 120 g of the title compound.Purity By GC: 98.41%.
	With ammonium acetate; sodium cyanoborohydride; In methanol; at 20℃; for 12h;	General procedure: 1-(2-methylphenyl)ethanone (0.50 mL, 3.73 mmol) and ammonium acetate (2.88 g, 37.3 mmol) were dissolved in methanol (20 mL). To the stirred solution was added slowly a solution of NaCNBH3 (0.79 g, 11.2 mmol) dissolved in methanol (15 mL) through a dropping funnel. The whole mixture was stirred at room temperature. After stirring for 12 h, solvent was removed by using rotary evaporator. The residue was dissolved in ethyl acetate and then the solution was treated with 6 N HCl solution to makethe solution to be acidic (pH = 12-13). The two layers were separated and then 6 N NaOH solutionwas added to the separated aqueous solution to make the solution to be basic (pH = 11-12). The basic aqueous solution was extracted with ethyl acetate twice and then combined organic solution was dried over anhydrous Na2SO4. Solvent was removed by using rotary evaporator to afford an intermediateamine B, 1-(2-methylphenyl)ethylamine (Ar = 2-methylphenyl, R1 = CH3, compound B in Figure 5) (0.21 g, 46% yield).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1310 - 1312
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6197 - 6208
[3]Patent: WO2008/58235,2008,A2 .Location in patent: Page/Page column 23-24
[4]Synthetic Communications,2011,vol. 41,p. 341 - 346
[5]Molecules,2014,vol. 19,p. 21386 - 21397
[6]European Journal of Organic Chemistry,2015,vol. 2015,p. 5393 - 5401

22
[ 17640-21-0 ]
[ 42882-31-5 ]
(R)-2-methoxy-N-[1-(naphthalen-1-yl)]acetamide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2007,p. 5416 - 5421

23
[ 344248-49-3 ]
[ 42882-31-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride; In ethanol; at 20℃; for 2h;	Gaseous hydrogen chloride was bubbled through a stirred solution of N-diphenylphosphinyl-1-naphthylethylamine in ethyl alcohol for 2 hours at room temperature. The reaction mixture was concentrated, made basic by the addition of an aqueous solution of sodium hydroxide (2 M) and extracted with dichloromethane (3×10 ml). The organic layer was washed with brine (1×10 ml), dried over magnesium sulphate and concentrated to give the product as a yellow liquid in 80% yield.

Reference： [1]Patent: US6696608,2004,B1 .Location in patent: Page column 28

24
N-diethylphosphinyl-1-naphthylethylamine [ No CAS ]
[ 42882-31-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With hydrogenchloride; In ethanol; at 20℃; for 2h;	Gaseous hydrogen chloride was bubbled through a stirred solution of N-diethylphosphinyl-1-naphthylethylamine in ethyl alcohol for 2 hours at room temperature. The reaction mixture was concentrated, made basic by the addition of an aqueous solution of sodium hydroxide (2 M) and extracted with dichloromethane (3×10 ml). The organic layer was washed with brine (1×10 ml), dried over magnesium sulphate and concentrated to give the product as a yellow liquid in 72% yield.

Reference： [1]Patent: US6696608,2004,B1 .Location in patent: Page column 29

25
[ 42882-31-5 ]
[ 198213-87-5 ]
N₁-(4-methoxybenzenesulfonyl)-N-2-[1-(1-naphthyl)ethyl]cyclohexane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In tetrahydrofuran; at 60℃; for 72h;	Synthesis of N1-(4-methoxybenzenesulfonyl)-N-2-[1-(1-naphthyl)ethyl]cyclohexane-1,2-diamine: PHD 263 To a solution of aziridine prepared beforehand (80 mg; 0.30 mmol) in 1 ml of tetrahydrofuran (THF), are successively added triethylamine (0.009 ml; 0.06 mmol) and 1-(1-naphthyl)ethylamine (0.145 ml; 0.90 mmol). After stirring for 3 days at 60 C., the medium is concentrated before being purified on a silica column (eluent: heptane/ethyl acetate: 1/1). 125 mg (0.285 mmol; 95%) of the compound of aziridine opening are isolated in the form of a colorless foam. The diamine is then converted to its hydrochloride by treatment with a solution of HCl in methanol. Mass spectrometry (ES): m/z: 439 [M+H]+ Melting point: 135-140 C. (decomposition)

Reference： [1]Patent: US2005/192317,2005,A1 .Location in patent: Page/Page column 7

26
[ 61293-10-5 ]
[ 42882-31-5 ]
[ 61082-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In chloroform; benzene;	EXAMPLE 10 d(+) and l(-) 3-[N-(1-{1-Naphthyl}ethyl)aminomethylene]-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester A mixture of 6.4 g. of racemic 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester from Example 7 and 3.2 g. of d-1-(1-naphthyl)ethylamine in 60 ml. of benzene are stirred at ambient temperature for 16 hrs. The solvent is removed by evaporation in vacuo, and the residue is redissolved in 250 ml. of chloroform. The chloroform solution is washed with 150 ml. of 1N sodium hydroxide, and then the dried organic phase is concentrated to dryness in vacuo. This affords 9.3 g. of 3-[N-(1-[1-naphthyl]ethyl)aminomethylene]-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester as a mixture of two diasteriomers, [alpha]D25 = -364.17 (1% solution in CHCl3).
	With sodium hydroxide; In chloroform; benzene;	A. d(+) and l(-) 3-[N-(1-{1-Naphthyl}ethyl)aminomethylene]-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester A mixture of 6.4 g. of racemic 3-hydroxymethylene-6,7-dimethoxy- 2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester from Example 1-F and 3.2 g. of d-1-(1-naphthyl)ethylamine in 60 ml. of benzene are stirred at ambient temperature for 16 hrs. The solvent is removed by evaporation in vacuo, and the residue is redissolved in 250 ml. of chloroform. The chloroform solution is washed with 150 ml. of 1N sodium hydroxide, and then the dried organic phase is concentrated to dryness in vacuo. This affords 9.3 g. of 3-[N-(1-[1-naphthyl]ethyl)aminomethylene]-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester as a mixture of two diasteriomers, [alpha]D25 = -364.17 (1% solution in CHCl3).

Reference： [1]Patent: US3976650,1976,A
[2]Patent: US3978064,1976,A

27
[ 7285-11-2 ]
[ 42882-31-5 ]
(R)-3-(2-chlorophenyl)-N-1-(naphthalene-1-yl)-propan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With hydrogenchloride; sodium hydroxide; diisobutylaluminium hydride; In dichloromethane;	Preparation of 12Z A stirred solution of 2-chlorohydrocinnamonitrile (Aldrich Chemical Co., 1.66 g, 10 mmol) in dichloromethane (100 ml) was cooled to -78 C. and treated dropwise with diisobutylaluminum hydride (1.42 g, 10 mmol). The reaction was stirred 1 hr at rt, cooled to -78 C. and treated with a solution of 1-(1-naphthyl)ethylamine (1.71 g, 10 mmol) in dichloromethane (25 ml). The reaction was transferred to an ice bath and stirred 2 hr. After this time the reaction was poured directly into a stirred solution of ethanolic sodium borohydride (50 ml of 0.2 M, 10 mmol). The mixture was stirred 30 min at rt and the excess sodium borohydride quenched by the addition of 10% HCl. The solution was then made basic by the addition of 10 N NaOH and transferred to a separatory funnel washing with diethyl ether (300 ml). The aqueous phase was removed and the remaining organic layer washed with 1 N NaOH (3*100 ml). The organic layer was dried over anhydrous magnesium sulfate, and concentrated to an oil. Chromatography of this material through silica gel using a gradient of chloroform to 10% methanol-chloroform afforded 2.34 g (72% yield) of (R)-N-[3-(2-chlorophenyl)propyl]-1-(1-naphthyl)ethylamine, 12Z, as a clear oil; m/z (rel. int.) 323 (M+, 2), 308 (63), 288 (7), 196 (5), 184 (5), 155 (100), 125 (24), 115 (8), 103 (4), 91 (3), 77 (7).

Reference： [1]Patent: US6211244,2001,B1

28
[ 42882-31-5 ]
[ 1821-12-1 ]
[1-(1-naphthyl)ethyl]-4-phenylbutyramide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 2673 - 2676

29
[ 17640-21-0 ]
[ 42882-31-5 ]
(R)-2-methoxy-N-[1-(naphthalen-1-yl)]acetamide [ No CAS ]
[ 10420-89-0 ]

Yield	Reaction Conditions	Operation in experiment
93%; 92%	With immobilized lipase B from Candida antarctica (Novozyme 435); In diethyl ether;	The racemate resolution of 1-(1-naphthyl)ethylamine was carried out as described by K. Ditrich (Synthesis 2008, 14; 2283-2287). 1-(1-Naphthyl)ethylamine (17.2 g, 0.1 mol) and isopropyl methoxyacetate (19.8 g, 0.15 mol) were dissolved in diethyl ether (400 ml). After addition of immobilized lipase B from Candida antarctica (Novozyme 435) (1 g), the turbid solution was stirred overnight at room temperature (30 rpm). The progress of the reaction was monitored by means of chiral HPLC. The reaction was stopped when an ee of 99.5% for the unreacted S-enantiomer and of 99.1% for the amide of the R-enantiomer was reached. Solid reaction residues were removed by filtration and washed with diethyl ether (50 ml). The combined filtrates were admixed with 5% strength aqueous HCl (50 ml) while stirring. After phase separation, the organic phase was washed with water (100 ml). The combined aqueous phases were reextracted with diethyl ether (3×70 ml) and the combined organic extracts were dried over sodium sulfate. After evaporation of the solvent and removal of unreacted isopropyl methoxyacetate by distillation, the amide of the R-enantiomer was obtained in the form of colorless crystals in a yield of 93%. An optically pure sample having a melting point of 80 C. could be obtained by recrystallization from cyclohexane. The combined aqueous extracts were made alkaline (pH 13) by addition of 50% strength aqueous NaOH while cooling in an ice bath. Diethyl ether (75 ml) was subsequently added and the phases were separated. The aqueous phase was extracted with diethyl ether (2×75 ml) and the combined extracts were dried over sodium sulfate. After evaporation of the solvent and purification by distillation, the S-enantiomer which remained was obtained in a yield of 92%.
48%; 45%	With Novozym 435; at 47℃;Molecular sieve; Enzymatic reaction;	General procedure: One of the amines rac-1a-i (2 mmol) and isopropyl methoxyacetate (2 mmol) were added into a reaction vessel containing Novozym 435 (25 mg) and molecular sieves (4 A, 50 mg). The reaction mixture was shaken (170 rpm) at room temperature (23 C) if not otherwise stated. The reaction was stopped by filtering off the enzyme at (50 +/- 0.5)% conversion. Isolation of the products was performed by silica gel chromatography using a mixture of hexane and ethylacetate and/or mixture of dichloromethane and methanol as eluent.

Reference： [1]Patent: US2013/345475,2013,A1 .Location in patent: Paragraph 0121
[2]Tetrahedron Asymmetry,2012,vol. 23,p. 230 - 236
[3]Synthesis,2008,p. 2283 - 2287

30
[ 1194019-76-5 ]
[ 42882-31-5 ]
[ 1194018-01-3 ]

Yield	Reaction Conditions	Operation in experiment
		l-(4-Fluoro-phenyl)-lH-indazole-4-carboxylic acid (40.0 mg, 0.156 mmol) and O-(J- azabenzotriazole-l-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (etaATU) (89 mg, 0.23 mmol) were combined in a 20 mL vial and dimethylacetamide (DMA) (1 mL) was added. The yellow solution was stirred at room temperature for 10 minutes and then a solution of l-(l-napthyl)ethylamine (40.1 mg, 0.234 mmol) and N-methylmorpholine (nuMM) (0.086 mL, 0.78 mmol) in DMA (0.20 mL) was added. The mixture was shaken at room temperature for 16 hours then the solution was evaporated in vacuo. The crude product was purified by preparative reversed-phase etaPLC to afford the title compound.

Reference： [1]Patent: WO2009/134666,2009,A1 .Location in patent: Page/Page column 55

31
[ 959138-87-5 ]
[ 42882-31-5 ]
[ 959132-55-9 ]

Yield	Reaction Conditions	Operation in experiment
35%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	Example 1862-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[(1S)-1-(1-naphthyl)ethyl]propionamide (Diastereomer A) 100.0 mg (0.325 mmol) of 2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-propionic acid from Example 105A are placed in 2 ml of DMF and treated with 61.2 mg (0.357 mmol) of (+/-)-1-(1-naphthyl)ethanamine, 52.7 mg (0.390 mmol) of HOBt and 81.0 mg (0.422 mmol) of EDC hydrochloride. The mixture is stirred overnight at room temperature, then partitioned between dichloromethane and water, and the organic phase is separated, dried over sodium sulphate and concentrated. The residue is purified by flash chromato-graphy on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 100:1) and then further separated by preparative HPLC on chiral phase [Method 15]. 52 mg (35% of theory) of the diastereomerically pure target compound are thus obtained (see also Example 187).MS [ESIpos]: m/z=461 (M+H)+. HPLC [Method 2]: Rt=4.84 min. chiral HPLC [Method 15]: Rt=2.49 min. 1H-NMR (400 MHz, DMSO-d6): delta=0.52 (m, 2H), 0.87 (m, 2H), 1.50 (d, 3H), 1.53 (d, 3H), 3.13 (tt, 1H), 4.80 (q, 1H), 5.68 (dq, 1H), 7.43 (t, 1H), 7.48-7.61 (m, 5H), 7.74 (d, 2H), 7.82 (d, 1H), 7.93 (m, 1H), 8.05 (m, 1H), 8.54 (d, 1H).

Reference： [1]Patent: US2009/312381,2009,A1 .Location in patent: Page/Page column 146

32
[ 63677-96-3 ]
[ 42882-31-5 ]
[ 949263-63-2 ]

Reference： [1]Chemical Communications,2009,p. 4566 - 4568

33
[ 42882-31-5 ]
[ 611-71-2 ]
[ 1073144-62-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol; at 25 - 60℃;	Example 4; Preparation of (R)-i-naphthylethylamine mandalate salt; Racemic 1-naphthylethylamine (2.63 moles, 450 gms) was suspended in ethanol (3.1 Its). D-mandelic acid (2.63 moles, 400 gms) was added under stirring. Pure (R)- naphthylethylamine mandalate (3-4 gms) was added as a seed and heated at 55-6O0C until a clear solution was obtained. The solution was cooled gradually to 25-3O0C and stirred for about 12 hours to obtain a solid. The solid was suspended in ethanol (2.3 Its) and heated at a temperature of 55-6O0C for about half an hour. The suspension was cooled gradually to 25-3O0C and stirred to obtain a solid. The solid was washed with ethanol and dried at 50-550C to obtain the title compound (250 gms, Yield 70%, chiral purity >;99.0%).

Reference： [1]Patent: WO2010/100429,2010,A1 .Location in patent: Page/Page column 20

34
[ 42882-31-5 ]
[ 611-71-2 ]
[ 1243166-48-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	In ethanol; at 25 - 60℃;	Example 5; Preparation of (S)-i-naphthylethylamine mandalate salt; Racemic 1-naphthylethylamine (2.63 moles, 450 gms) was suspended in isopropyl alcohol (3.1 Its). D-mandelic acid (1.32 moles, 200 gms) was added under stirring and heated at 55-6O0C until a clear solution was obtained. The solution was cooled gradually to 25-3O0C and stirred for about 12 hours to obtain a solid. The solid was suspended in isopropyl alcohol (2.3 Its) and heated at a temperature of 55-6O0C for about half an hour. The suspension was cooled gradually to 25-3O0C and stirred to obtain a solid. The solid was washed with isopropyl alcohol and dried at 50-550C to obtain the title compound (225 gms, Yield 62%, chiral purity >;99.0%).

Reference： [1]Patent: WO2010/100429,2010,A1 .Location in patent: Page/Page column 20

35
[ 42882-31-5 ]
[ 84358-13-4 ]
[ 1090622-85-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In acetonitrile; at 50℃;	Example 123: Preparation of l-[7-chloro-2-(2-chIoro-6-fluoro-phenyl)-lH- benzimidazole-5-carbonyl]-piperidine-4-carboxylic acid (1-naphthalen-l-yl-ethyl)- amide; The title compound was prepared as follows:; Step 1 : Preparation of 4-(l-naphthalen-2-yl-ethylcarbamoyl)-piperidine-l- carboxylic acid tert-butyl ester; To a solution piperidine-l,4-dicarboxylic acid mono-tert-butyl ester (0.30 g, 1.30 mmol) in acetonitrile was added DCC(0.26g, 1.30 mmol) and HOBT (0.19g, 1.43 mmol), 1-naphthalen-l-yl-ethylamine (0.25 ml, 1.57 mmol). This reaction mixture was stirred overnight at 50 C , then the solvent was evaporated, and the residue stirred with sat- NaHC03(aq) solution was added, and the mixture was then extracted with ethyl acetate. The organic phase was separated, dried over Na2S04 and concentrated in vacuo. Purification of the residue by silica gel chromatography (Hex/EA=2/1) to give the title compound: 0.45 g (92 %). NMR (DMSO-d6, 300 MHz) : 6(ppm) 8.05-7.43 (m, 7H), 5.87 (q, J=8.5 Hz, 1 H), 2.75-1.60 (m, 8H), 1.67 (d, J=7.5 Hz, 3H), 1.43 (s, 9H)

Reference： [1]Patent: WO2011/99832,2011,A2 .Location in patent: Page/Page column 112-113

36
[ 173459-03-5 ]
[ 42882-31-5 ]
[ 1350639-72-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	In butan-1-ol; at 145℃; for 24h;Inert atmosphere;	General procedure: The following is representative: 4-chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine (7a) (275 mg, 1.06 mmol) and (R)-1-phenylethanamine (0.44 mL, ?3.5 mmol) were added to a dry round bottle flask containing 1-butanol (3.5 mL) under argon atmosphere. The mixture was heated at 145 C for 24 h. The precipitate formed upon cooling to rt. was isolated by filtration, washed with diethyl ether (25 mL) and dried resulting in a solid.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 6002 - 6014

37
[ 42882-31-5 ]
[ 158966-92-8 ]
[ 1380816-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate at 25 - 30℃; for 10h;	7 Example 7: Preparation of montelukast l-(l-naphthyl)ethylamine saltMethod A: To a stirred solution of montelukast (98 g, 0.16 mol) in ethyl acetate (400 ml), 1-(1- naphthyl)ethylamine salt (38 g, 0.22 mol) was added at 25-30 °C and was stirred for 10 hours. The precipitated solid was filtered off. Acetonitrile (1000 ml) was slowly added to resulting filtrate at 25- 30 °C and stirred for 24 hours. The precipitated solid was filtered and washed successively with acetonitrile (200 ml) and n-heptane (200 ml). The resulting solid was dried for 2 hours and dried under vacuum at 30 °C for 4 hours to give 70 g of crystalline title compound having purity 99.3 % by HPLC.

Reference： [1]Current Patent Assignee: IND-SWIFT LABORATORIES LIMITED - WO2012/77133, 2012, A1 Location in patent: Page/Page column 24-25

38
[ 42882-31-5 ]
[ 807638-71-7 ]
[ 162515-68-6 ]
[ 1380816-64-7 ]

Yield	Reaction Conditions	Operation in experiment
		Method B: A solution of l-(mercaptomethyl)cyclopropaneacetic acid (30 g ,0.21 mol) in methanol (30 ml) was added to a cooled solution of methanolic sodium hydroxide (prepared by dissolving sodium hydroxide (18 g ,0.45 mol ) in methanol (120 ml ) and stirred for 5 hours at ambient temperature. Tetrahydrofuran (500 ml) was added to the reaction mixture and cooled to -15 to -10 C. [(S)-(E)]-2-[2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl] phenyl]-3-methanesulphonyloxy]propyl] phenyl] -2-propanol (obtained as above) was added to above reaction mixture at -15 to -10 C and temperature of the reaction mixture was slowly raised to 25-30 C. The reaction mixture was stirred for 15 hours at 25-30 C. After completion of reaction, demineralized water (500 ml) was added to the reaction mixture followed by addition of 10 % tartaric acid to adjust the pH of reaction mixture to 9-10 and extracted with n-heptane (3 x 800ml). Another portion of 10 % tartaric acid (180 ml) was added to reaction mixture and aqueous layer was extracted with dichloromethane (2 x 500 ml) and the combined organic layer was successively washed with 2% sodium bicarbonate solution (500 ml) and water (2 x 500 ml). Butylated hydroxy anisole (2 g), activated charcoal (20 g) and anhydrous sodium sulfate were added to dichloromethane layer at 25-30 C and stirred for 30 minutes. Reaction mixture was filtered through hyflo-bed. dichloromethane was partially distilled off from reaction mixture and resulting reaction mixture was cooled to ambient temperature. Acetonitrile (400 ml) was added to reaction mixture and stirred for 1 hour. The reaction mixture was then heated to 35-40 C and l-(l-naphthyl)ethyl amine (35 g) followed by acetonitrile (600 ml) were successively added to reaction mixture and stirred for 12 hours. The solid thus precipitated was filtered, successively washed with acetonitrile (200 ml ) and n-heptane (200ml) and dried to give 85.3g of title compound. A portion of resulting product was purified using dichloromethane and acetonitrile to give purified title compound which was again purified with water, methanol and acetonitrile to give title compound having purity 99.84 % by HPLC and melting point: 100.20 C by DSC.

Reference： [1]Patent: WO2012/77133,2012,A1 .Location in patent: Page/Page column 25

39
[ 42882-31-5 ]
[ 75-36-5 ]
[ 72407-64-8 ]
[ 82796-68-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 0.25h;	General procedure: (S)-1-Phenylethylamine and (R)-phenylethylamine were mixed in a ratio of 85/15. To the mixture (242 mg, 2.0 mmol) in THF (6.0 mL) were added Et3N (0.42 mL, 3.0 mmol) and acetyl chloride (0.14 mL, 2.0 mmol) at 0 C. After being stirred for 15 min at rt, the mixture was poured into NH4Cl aq and extracted with AcOEt. The AcOEt extracts were washed with brine, dried over MgSO4, and evaporated to dryness. Purification of the residue by column chromatography (hexane/AcOEt=1) gave 1a (319 mg, 98%).

Reference： [1]Tetrahedron,2012,vol. 68,p. 4013 - 4017

40
[ 42882-31-5 ]
[ 610-10-6 ]
[ 40138-16-7 ]
C₆H₄BCHNCHCH₃C₁₀H₇C₆H₁₀(CO₂)2 [ No CAS ]
C₆H₄BCHNCHCH₃C₁₀H₇C₆H₁₀(CO₂)2 [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6410 - 6419

41
(3-fluoro-2-formylphenyl)boronic acid [ No CAS ]
[ 42882-31-5 ]
[ 610-10-6 ]
C₆H₃FBCHNCHCH₃C₁₀H₇C₆H₁₀(CO₂)2 [ No CAS ]
C₆H₃FBCHNCHCH₃C₁₀H₇C₆H₁₀(CO₂)2 [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6410 - 6419

42
(3-fluoro-2-formylphenyl)boronic acid [ No CAS ]
[ 46022-05-3 ]
[ 42882-31-5 ]
C₂₇H₂₅BFNO₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6410 - 6419

43
[ 46022-05-3 ]
[ 42882-31-5 ]
[ 40138-16-7 ]
C₂₇H₂₆BNO₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6410 - 6419

44
[ 42882-31-5 ]
[ 226256-56-0 ]

Reference： [1]Patent: WO2014/178068,2014,A2
[2]Patent: CN104592037,2016,B

45
[ 42882-31-5 ]
[ 287714-41-4 ]
[ 1416820-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate; at 0 - 20℃; for 10.5h;	A mixture of <strong>[287714-41-4]rosuvastatin</strong> (60 g) in ethyl acetate (300 ml) was cooled to 0C and a solution of (+)-l-(l-naphthyl)ethylamine (21 g) in ethyl acetate (60 ml) was added. Reaction mixture was stirred for 30 minutes at same temperature. Thereafter; temperature of reaction mixture was raised to ambient temperature and stirred for further 10 hours. n-Heptane (240 ml) was added to the reaction mixture to induce precipitation. Reaction mixture was cooled to -10 C and stirred for 1 hour at same temperature. Product, thus formed, was filtered, washed with n-heptane and ethyl acetate mixture and dried to give 60 g of title compound having purity 96.5 % by HPLC

Reference： [1]Patent: WO2012/176218,2012,A1 .Location in patent: Page/Page column 22

46
[ 42882-31-5 ]
[ 147118-40-9 ]
[ 1416820-70-6 ]

Yield	Reaction Conditions	Operation in experiment
		7- [4-(4-Fluoro-phenyl)-6-isopropyl-2-(methanesulfonyl-n ethyl-amino)- pyrimidin-5-yl]-3,5-dihydroxy-hept-6-enoic acid methyl ester (500 g) was treated with aqueous sodium hydroxide ( 60 g sodium hydroxide in 2.5 L water ) and stirred the reaction mass at 25-35 °C for 1-2 hours. After completion of reaction, reaction mass was cooled to ambient temperature and activated carbon (25 g) was added and stirred for 30 minutes. Reaction mixture was filtered through hyflow bed and wash bed with water. Resulting filtrate was washed with methyl tert-butyl ether (4 x 1.5 L). Ethyl acetate (2.5 L) was added to resulting mixture followed by addition of concentrated hydrochloric acid to adjust pH of reaction mixture 1 to 2 at 10-15 °C and stirred. Layers were separated and aqueous layer was re-extracted with ethyl acetate (1 L). Combined organic layer was washed with brine solution. (+)-l-(l-naphthyl)ethylamine (175 g) diluted with ethyl acetate (250 ml) was added to the resulting organic layer to adjust the pH of reaction mixture to 7- 8. Solvent was distilled off completely from the reaction mixture. Ethyl acetate (2.5 L) was added to resulting residue followed by addition of (+)-l-(l-naphthyl)ethylamine (170 g) diluted with ethyl acetate (250 ml) and stirred for 6-8 hours at ambient temperature. n-Heptane (1.5 L ml) was added to resulting mixture and cooled the mixture at -5 °C. Resulting reaction mixture was stirred for 1 hour, filtered, washed with n-heptane. Resulting wet product was slurried in acetonitrile (2.5 L), filtered, washed with acetonitrile (250 ml) and dried to give 310 g of title compound having purity 99.74 percent; anti-isomer: 0.2 percent; lactone: not detected; 5-keto acid impurity: not detected by HPLC.

Reference： [1]Patent: WO2012/176218,2012,A1 .Location in patent: Page/Page column 22

47
[ 42882-31-5 ]
[ 3282-30-2 ]
[ 168104-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In cyclohexane; at 10℃; for 6h;	General procedure: The N-acylation of racemic 1, 2, and 3 was carried out with acyl chlorides as acylation reagents and triethylamine as the base in cyclohexane in the presence and absence of TIPS-beta-CD. After a mixture of racemic 1, 2, and 3 (6.0x10-4 mmol) and 6-O-silylated beta-CD was stirred for 1 h in cyclohexane (600 muL) to reach the complexation equilibrium between 1, 2, and 3 and 6-O-silylated beta-CD, triethylamine (6.0x10-4 mmol), the acyl chlorides 4a-j were added at 10 C. The mixture was then stirred at 10 C for 6 h. The resulting products were analyzed by HPLC using the chiral phase column Diacel Chiralcel OD-H (250mm x4.6mm i.d.) using hexane/2-propanol=80:20 or 95:5 as an eluent at a flow rate of 0.5 or 1.5 mL min-1 using UV detection (254 nm). The HPLC charts of the products obtained after N-acylation of 1, 2, and 3 (6.0x10-4 mmol) with acyl chlorides 4a-j (3.3x10-4 mmol) in cyclohexane (600 muL)including triethylamine (6.0x10-4 mmol) in the absence and presence of TIPS-beta-CD (3.0x10-3 mmol) are shown in Figs. S18-26,respectively