79389-41-6|(1R,2S)-2-Methylcyclohexylamine Hydrochloride| Ambeed

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Quality Control of [ 79389-41-6 ] Purity: 95% SDS Specification

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Product Details of [ 79389-41-6 ]

CAS No. :	79389-41-6
Formula :	C₇H₁₆ClN
M.W :	149.66
SMILES Code :	N[C@H]1[C@@H](C)CCCC1.[H]Cl
MDL No. :	MFCD22201094
InChI Key :	XCLFCWFKPOQAHM-UOERWJHTSA-N
Pubchem ID :	12714250

Safety of [ 79389-41-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 79389-41-6 ]

* 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.

Downstream synthetic route of [ 79389-41-6 ]

[ 79389-41-6 ] Synthesis Path-Downstream 1~17

1
[ 3886-69-9 ]
[ 583-60-8 ]
[ 79389-41-6 ]

References: [1]Chemische Berichte,1984,vol. 117,p. 2076 - 2098.

2
[ 91603-25-7 ]
[ 79389-41-6 ]

Yield	Reaction Conditions	Operation in experiment
51.4%	With hydrogen;palladium 10% on activated carbon; In ethanol; under 2585.81 Torr; for 24h;	To a solution of (li?,21S)-2-Methyl-N-((i?)-l-phenylethyl)cyclohexanamine hydrochloride (2Od) (3.99 g) in EtOH (45 mL) was added Pd/C (10%) (750 mg) and hydrogenated at 50 psi for 24 h. The catalyst was removed by filtration through celite and filtrate concentrated in vacuum to give 2.3g of white solid, which was recrystallized from EtOH/ether, to give (R,2S)-2- Methylcyclohexanamine hydrochloride (2Oe) (1.35 g, 51.4 %) as an off-white solid; mp 241.9 0C; 1H NMR (300 MHz, DMSO) δ 8.13 (s, 3H), 3.20-3.08 (m, IH), 1.99 (m, IH), 1.63 (m, 3H), 1.44 (m, 3H), 1.31 (m, 2H), 0.92 (d, J= 7.1 Hz, 3H). MS (ES+) 114.3 (M+l); Optical rotation: [α] =+7.97 (c=l.18, EtOH); Analysis: Calcd for C7H15N• HCl: C, 56.18; H, 10.78; N, 9.36; Cl, 23.69; Found: C, 56.06; H, 10.98; N, 9.21; Cl, 23.47.

References: [1]Patent: WO2011/14817,2011,A1 .Location in patent: Page/Page column 98.
[2]Chemische Berichte,1984,vol. 117,p. 2076 - 2098.

3
[ 15761-39-4 ]
[ 79389-41-6 ]
BOC-(S)-proline-(1R,2S)-2-methylcyclohexylamide [ No CAS ]

References: [1]Journal of Catalysis,1999,vol. 185,p. 479 - 486.

4
[ 79389-41-6 ]
(S)-3-Benzyloxycarbonylamino-N-((R)-2-isobutoxycarbonyloxy-1-methyl-2-oxo-ethyl)-succinamic acid benzyl ester [ No CAS ]
[ 302596-11-8 ]

References: [1]Scientia Pharmaceutica,2000,vol. 68,p. 165 - 172.

5
[ 79389-41-6 ]
(S)-proline-(1R,2S)-2-methylcyclohexylamide [ No CAS ]

References: [1]Journal of Catalysis,1999,vol. 185,p. 479 - 486.

6
[ 75-44-5 ]
[ 1228449-72-6 ]
[ 79389-41-6 ]
[ 1228450-95-0 ]

Yield	Reaction Conditions	Operation in experiment
65%		Step 1 Variation A (S)-3-amino-piperidine-1-carboxylic acid tert-butyl ester (0.1 g, 0.378 mmol) was dissolved in DCM (3 mL). N,N-diisopropylethylamine (0.23 mL, 1.324 mmol) was added and the resulting light yellow solution was cooled by a NaCl/ice bath. After about 20 minutes phosgene 20% in toluene (0.24 mL, 0.454 mmol) was added. After about 20 minutes (1R,2S)-2-methyl-cyclohexylamine hydrochloride (0.068 g, 0.454 mmol) was added. The resulting mixture was stirred in the NaCl/ice bath for an hour. 1 mL of MeOH was added and the mixture was allowed to warm up to RT before being evaporated. The remaining oil was partitioned between DCM and H2O. The aqueous layer was extracted twice with DCM, the organic layers were combined, dried over Na2SO4, filtered and evaporated. The residue was purified by SiO2 chromatography (24 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100 to 83% DCM) to give 0.1 g of 1-((1R,2S)-2-methyl-cyclohexyl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as a light brown solid (65% yield).

References: [1]Patent: US2010/144745,2010,A1 .Location in patent: Page/Page column 53.

7
cis (2-methyl-cyclohexyl)-((R)-1-phenyl-ethyl)-amine [ No CAS ]
[ 79389-41-6 ]

Yield	Reaction Conditions	Operation in experiment
16%		Step 2: To cis (2-methyl-cyclohexyl)-((R)-1-phenyl-ethyl)-amine (0.65 g, 2.99 mmol) Pd(OH)2 on carbon 20 wt % (0.3 g) and EtOH (10 mL) were added and the reaction mixture stirred at RT under 1 atm of H2 overnight. The palladium was filtered off and the solvent was evaporated (be careful, the free amine sublimes). The remaining material was purified by SiO2 chromatography (40 g SiO2, DCM/(DCM:MeOH:NH4OH 60:10:1) 100-71% DCM). TLC shows only one major spot. Ten fractions were evaporated at a time. After running NMR the first 20 were combined and evaporated. The residue was dissolved in DCM and treated with 4M HCl in dioxane. The solvent was evaporated and the remaining solid was dried under high vacuum to give 0.075 g of (1R,2S)-2-methyl-cyclohexylamine hydrochloride as an off-white solid (16% yield). NMR showed the presence of about 5% of the trans isomer.

References: [1]Patent: US2010/144745,2010,A1 .Location in patent: Page/Page column 42.

8
[ 583-60-8 ]
[ 79389-41-6 ]

References: [1]Patent: WO2011/14817,2011,A1 .

9
[ 79389-41-6 ]
[ 1263419-23-3 ]

References: [1]Patent: WO2011/14817,2011,A1 .

10
[ 79389-41-6 ]
[ 1263419-24-4 ]

References: [1]Patent: WO2011/14817,2011,A1 .

11
[ 1263420-00-3 ]
[ 79389-41-6 ]
[ 1263419-13-1 ]

References: [1]Patent: WO2011/14817,2011,A1 .

12
[ 1263420-00-3 ]
[ 79389-41-6 ]
[ 1263420-10-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 15h;	To a solution of 4-chloropyrrolo[l,2-b]pyridazine-3-carbonitrile (15g) (80 mg, 0.45 mmol) in DMF (10 mL) was added (lR,2S)-2-methylcyclohexanamine Hydrochloride (2Oe) (180 mg, 1.20 mmol), triethylamine (0.51 mL, 3.66 mmol) and stirred at room temperature for 15 h. The reaction mixture was diluted with EtOAc (100 mL), washed with water (2 x 50 mL), brine (50 mL), dried over MgSO4, filtrated and the concentrated in vacuum. The residue was purified by flash column chromatography [silica gel, 30 g eluting with hexanes/ethyl acetate, 1 :0 to 6:1 (Rf = 0.46 hexanes/ethyl acetate = 6:1)] to afford 4-((lR,2S)-2- methylcyclohexylamino)pyrrolo[l,2-b]pyridazine-3-carboxamide (18f) (0.105 g, 92%) as a light green oil; 1U NMR (300 MHz, DMSO-^6): δ 7.90 (s, IH), 7.70 (dd, J= 1.6, 2.6 Hz, IH), 7.34 (s, IH), 7.32 (dd, J= 1.6, 4.5 Hz, IH), 6.68 (dd, J= 2.7, 4.4 Hz, IH), 4.46-4.33 (m, IH), 2.32-2.19 (m, IH), 1.88 - 1.33 (m, 8H), 0.91 (d, J= 7.1 Hz, 3H); MS (ES"): 253.0 (M-I).

References: [1]Patent: WO2011/14817,2011,A1 .Location in patent: Page/Page column 98.

13
[ 1263420-15-0 ]
[ 79389-41-6 ]
[ 1263419-22-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	To a solution of 4-chloro-6-nitropyrrolo[l,2-b]pyridazine-3-carbonitrile (47d) (180 mg, 0.81 mmol) in DMF (20 mL) was added (lR,2S)-2-methylcyclohexanamine hydrochloride (2Oe) (320 mg, 2.14 mmol) triethylamine (0.90 mL, 6.46 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (150 mL), washed with water (2 x 75 mL), brine (50 mL), dried over MgSO4 filtered and concentrated in vacuum to dryness. The residue obtained was purified by flash column chromatography [silica gel 12g, eluting with hexanes/ethyl acetate, 1 :0 to 5:1, (Rf = 0.46 with hexanes/ethyl acetate = 5:1)] to afford 4- (( 1 R,2S)-2-methylcyclohexylamino)-6-nitropyrrolo [ 1 ,2-b]pyridazine-3 -carbonitrile (48d) (228 mg, 94%) as a yellow solid; 1H NMR (300 MHz, OMSO-d6): δ 8.68 (d, J= 2.0 Hz, IH), 8.18 (s, IH), 8.16 (d, J= 1.9 Hz, IH), 7.97 (d, J= 7.9 Hz, IH), 4.48-4.36 (m, IH), 2.34-2.22 (m, IH), 1.91 - 1.29 (m, 8H), 0.93 (d, J= 7.1 Hz, 3H); MS (ES"): 297.9 (M-I).

References: [1]Patent: WO2011/14817,2011,A1 .Location in patent: Page/Page column 106; 107.

14
(R,Z)-N-(2-methylcyclohexylidene)-1-phenylethaneamine [ No CAS ]
[ 79389-41-6 ]

References: [1]Patent: WO2011/14817,2011,A1 .

15
[ 31887-88-4 ]
[ 79389-41-6 ]
[ 79389-39-2 ]

References: [1]Tetrahedron Asymmetry,2014,vol. 25,p. 238 - 244.

16
[ 1071759-20-0 ]
[ 79389-41-6 ]
[ 79389-39-2 ]

Yield	Reaction Conditions	Operation in experiment
		N-[(1R,2S)-2-Methylcyclohexyl]-benzenemethanamine 3 (0.110 g, 0.54 mmol) was deprotected using an H-Cube [80 C, 80 bar, Pd(OH)2/C] in ethanol (20 mL) with a few drops of acetic acid for 4 h. After evaporation, the amine was dissolved in Et2O (3 mL) and added to a premixed solution of trimethylacetyl chloride (0.2 mL, 1.62 mmol) and ethanol (0.09 mL, 1.62 mmol) in Et2O (10 mL). The precipitate formed was filtered to give (1R,2S)-2-methylcyclohexanamine hydrochloride salt 5 as a pale white solid (0.032 g, 40%). Mp 234 C (lit.6 241.9 C); (c 0.65, EtOH, assumed 77% ee), lit.6 (c 1.18, EtOH, 100% ee); ν(max)/cm-1 2859, 2933, 1606, 1587, 1509; δH (400 MHz, DMSO) 0.91 (3H, d, J 6.2, CH3), 1.31-1.35 (2H, m, CH2), 1.41-1.49 (3H, m, CH2), 1.58-1.68 (3H, m, CH2), 1.92-2.02 (1H, m, CH3CH), 3.11-3.19 (1H, m, NCH), 8.02 (3H, br s, CHNH3); δC (100 MHz, DMSO) 14.0 (CH3), 21.0 (CH2), 22.1 (CH2), 26.1 (CH2), 29.4 (CH2), 31.1 (CH3CH), 52.5 (NH2CH); m/z (TOF ES+) 114.1282 (100%, MH+-Cl, C7H16N requires 114.1283). No mass spectrometry or 13C NMR data was reported in the literature.

References: [1]Tetrahedron Asymmetry,2014,vol. 25,p. 238 - 244.

17
[ 583-60-8 ]
[ 79389-41-6 ]
[ 79389-39-2 ]

References: [1]Tetrahedron Asymmetry,2014,vol. 25,p. 238 - 244.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Halogenation • Heat of Combustion • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

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[ 79389-41-6 ]

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CAS No.: 79389-41-6

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