[ CAS No. 4152-92-5 ] {[proInfo.proName]}

Name: 4152-92-5|(2-(Aminomethyl)phenyl)methanol|97%
Brand: Ambeed
SKU: A100100
Price: 9.0 USD
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Quality Control of [ 4152-92-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4152-92-5 ]

Product Details of [ 4152-92-5 ]

CAS No. :	4152-92-5	MDL No. :	MFCD09035091
Formula :	C₈H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FTFHSGKASINZBY-UHFFFAOYSA-N
M.W :	137.18	Pubchem ID :	11275036
Synonyms :

Calculated chemistry of [ 4152-92-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.24
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	-0.11
Log Po/w (WLOGP) :	0.33
Log Po/w (MLOGP) :	0.94
Log Po/w (SILICOS-IT) :	1.28
Consensus Log Po/w :	0.8

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.93
Solubility :	16.0 mg/ml ; 0.117 mol/l
Class :	Very soluble
Log S (Ali) :	-0.41
Solubility :	53.6 mg/ml ; 0.391 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.24
Solubility :	0.784 mg/ml ; 0.00571 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 4152-92-5 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P264-P270-P280-P305+P351+P338-P310-P330-P501	UN#:	N/A
Hazard Statements:	H302-H318	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4152-92-5 ]

* 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 [ 4152-92-5 ]
Downstream synthetic route of [ 4152-92-5 ]

[ 4152-92-5 ] Synthesis Path-Upstream 1~13

1
[ 7468-67-9 ]
[ 4152-92-5 ]

Reference： [1] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17366 - 17369
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 23, p. 5568 - 5570
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 11, p. 3821 - 3839
[4] Angewandte Chemie - International Edition, 2010, vol. 49, # 37, p. 6633 - 6637
[5] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[6] Patent: US5698560, 1997, A,
[7] Organic Letters, 2016, vol. 18, # 4, p. 642 - 645
[8] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13351 - 13355[9] Angew. Chem., 2017, vol. 129, p. 13536 - 13540,5

2
[ 6538-31-4 ]
[ 75-05-8 ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1] Russian Journal of General Chemistry, 2001, vol. 71, # 1, p. 150 - 150

3
[ 75-05-8 ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 2001, vol. 37, # 1, p. 129 - 130

4
[ 75-05-8 ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 2001, vol. 37, # 1, p. 129 - 130

5
[ 75-05-8 ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 2001, vol. 37, # 1, p. 129 - 130

6
[ 359010-73-4 ]
[ 4152-92-5 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 2001, vol. 37, # 1, p. 129 - 130
[2] Russian Journal of Organic Chemistry, 2001, vol. 37, # 2, p. 295 - 296

7
[ 6587-24-2 ]
[ 4152-92-5 ]

Reference： [1] Gazzetta Chimica Italiana, 1966, vol. 96, p. 1671 - 1695

8
[ 7115-95-9 ]
[ 4152-92-5 ]

Reference： [1] Gazzetta Chimica Italiana, 1966, vol. 96, p. 1671 - 1695

9
[ 14859-23-5 ]
[ 4152-92-5 ]

Reference： [1] Gazzetta Chimica Italiana, 1966, vol. 96, p. 1671 - 1695

10
[ 14758-57-7 ]
[ 4152-92-5 ]

Reference： [1] Gazzetta Chimica Italiana, 1966, vol. 96, p. 1671 - 1695

11
[ 91-13-4 ]
[ 4152-92-5 ]

Reference： [1] Gazzetta Chimica Italiana, 1966, vol. 96, p. 1671 - 1695

12
[ 50-00-0 ]
[ 7732-18-5 ]
[ 100-46-9 ]
[ 4152-92-5 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1895, vol. <3>13, p. 157[2] Chemische Berichte, 28 Ref. <1895>,852,

13
[ 4152-92-5 ]
[ 32372-82-0 ]

Reference： [1] Organic Syntheses, 2013, vol. 90, p. 251 - 260

[ 4152-92-5 ] Synthesis Path-Downstream 1~87

1
[ 75-44-5 ]
[ 4152-92-5 ]
[ 39976-24-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1972,vol. 9,p. 1209 - 1214

2
[ 6587-24-2 ]
[ 4152-92-5 ]

Reference： [1]Gazzetta Chimica Italiana,1966,vol. 96,p. 1671 - 1695

3
[ 4152-92-5 ]
[ 545-06-2 ]
[ 60523-78-6 ]

Reference： [1]Journal of Medicinal Chemistry,1978,vol. 21,p. 1283 - 1290

4
[ 7115-95-9 ]
[ 4152-92-5 ]

Reference： [1]Gazzetta Chimica Italiana,1966,vol. 96,p. 1671 - 1695

5
[ 14859-23-5 ]
[ 4152-92-5 ]

Reference： [1]Gazzetta Chimica Italiana,1966,vol. 96,p. 1671 - 1695

6
[ 624-01-1 ]
[ 4152-92-5 ]
11a-Pentyl-1,2,3,5,10,11a-hexahydro-11-oxa-4a-aza-dibenzo[a,d]cyclohepten-4-one [ No CAS ]

Reference： [1]Synlett,1999,p. 37 - 40

7
[ 4152-92-5 ]
3-(2-bromoethyl)cyclohexanone ethylene ketal [ No CAS ]
[ 198127-14-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8280 - 8281

8
[ 50-00-0 ]
[ 7732-18-5 ]
[ 100-46-9 ]
[ 4152-92-5 ]

Reference： [1]Bulletin de la Societe Chimique de France,1895,vol. <3>13,p. 157
Chemische Berichte, 28 Ref. <1895>,852,

Yield	Reaction Conditions	Operation in experiment
		2-Hydroxymethylbenzylamine Lithium aluminium hydride (12.4 ml, 1.0M in diethyl ether) was added cautiously to 2-cyanomethylbenzoate (1.00 g, 6.2 mmol) in anhydrous diethyl ether (40 ml) under nitrogen with stirring over 10min. whilst ensuring the temperature was not greater than 15-25 C. using an ice bath. After the addition was complete the reaction mixture was allowed to warm to 21 C. and then heated at reflux for 16 h. The reaction mixture was cooled to approximately -10 C. It was treated cautiously dropwise with water (0.5 ml), 20% aqueous sodium hydroxide (0.37 ml) and water (1.74 ml). The resultant green heterogeous mixture was filtered and the residue was with diethyl ether (150 ml), the combined washings and filtrate were dried (MgSO4) and solvent was removed in vacuo affording the title compound as a green oil (0.807 g). Mass Spectrum m/z 138 (MH+for C8H12NO).

11
[ 41269-05-0 ]
[ 4152-92-5 ]
2-isopropyl-5,6-benzo-1,3,2-oxazaborepane [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 817 - 818

12
[ 4152-92-5 ]
[ 118577-44-9 ]
[ 397870-14-3 ]

Reference： [1]Synlett,2001,p. 1506 - 1510

13
[ 4152-92-5 ]
[ 397870-12-1 ]
[ 397870-15-4 ]

Reference： [1]Synlett,2001,p. 1506 - 1510

14
[ 4152-92-5 ]
[ 397870-18-7 ]
[ 397870-19-8 ]

Reference： [1]Synlett,2001,p. 1506 - 1510

15
[ 6538-31-4 ]
[ 75-05-8 ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 150 - 150

16
[ 75-05-8 ]
2-Ethyl-5,6-benzo-1,3,2-dioxaborepane [ No CAS ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 129 - 130

17
[ 75-05-8 ]
2-Isopropyl-5,6-benzo-1,3,2-dioxaborepane [ No CAS ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 129 - 130

18
[ 75-05-8 ]
2-Isobutoxy-5,6-benzo-1,3,2-dioxaborepane [ No CAS ]
[ 4152-92-5 ]
[ 359010-73-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 129 - 130

19
[ 359010-73-4 ]
[ 4152-92-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 129 - 130
[2]Russian Journal of Organic Chemistry,2001,vol. 37,p. 295 - 296

20
[ 7468-67-9 ]
[ 4152-92-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	REFERENCE EXAMPLE 3 2-(Hydroxymethyl)benzylamine Lithium aluminium hydride (17.4 g, 458 mmol) was suspended in dried tetrahydrofuran (300 ml), followed by stirring under ice-cooling in an argon atmosphere. A solution of 2-cyanobenzaldehyde (20.0 g, 153 mmol) dissolved in dried tetrahydrofuran (100 ml) was dropwise and portionwise added thereto and the reaction solution was stirred for 3 hours under heating at reflux. After the reaction, the solution was ice-cooled and sodium sulfate 10 hydrate was portionwise added thereto until foaming and fever ceased. The reaction solution was filtered and the filtrate was concentrated to give the title compound (20.9 g, quantitative) as oily substances. This compound was used in the subsequent reaction without further purification.

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 17366 - 17369
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 5568 - 5570
[3]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3821 - 3839
[4]Angewandte Chemie - International Edition,2010,vol. 49,p. 6633 - 6637
[5]Chemistry - A European Journal,2012,vol. 18,p. 1383 - 1400
[6]Patent: US5698560,1997,A
[7]Organic Letters,2016,vol. 18,p. 642 - 645
[8]Angewandte Chemie - International Edition,2017,vol. 56,p. 13351 - 13355
Angew. Chem.,2017,vol. 129,p. 13536 - 13540,5
[9]Journal of the American Chemical Society,2020,vol. 142,p. 3636 - 3644

21
[ 4152-92-5 ]
[ 123-11-5 ]
[ 871913-12-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3821 - 3839

22
[ 2483-46-7 ]
[ 4152-92-5 ]
C₂₄H₃₉N₃O₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5568 - 5570

23
[ 2389-45-9 ]
[ 4152-92-5 ]
tert-butyl (S)-6-(N-benzyloxycarbonyl)amino-1-(2-(hydroxymethyl)benzylamino)-1-oxohexan-2-ylcarbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5568 - 5570

24
[ 13139-16-7 ]
[ 4152-92-5 ]
tert-butyl (2S,3S)-1-(2-(hydroxymethyl)benzylamino)-3-methyl-1-oxopentan-2-ylcarbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5568 - 5570

25
[ 13139-16-7 ]
[ 4152-92-5 ]
tert-butyl (2S,3R)-1-(2-(hydroxymethyl)benzylamino)-3-methyl-1-oxopentan-2-ylcarbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5568 - 5570

26
[ 4152-92-5 ]
{2-[(4-chloro-phenyl)-phenyl-methoxymethyl]-benzyl}-(4-methoxy-benzyl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3821 - 3839

27
2-Ethyl-5,6-benzo-1,3,2-dioxaborepane [ No CAS ]
[ 4152-92-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 129 - 130

28
2-Isopropyl-5,6-benzo-1,3,2-dioxaborepane [ No CAS ]
[ 4152-92-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 129 - 130

29
2-Isobutoxy-5,6-benzo-1,3,2-dioxaborepane [ No CAS ]
[ 4152-92-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 129 - 130

30
[ 4152-92-5 ]
[ 397870-25-6 ]

Reference： [1]Synlett,2001,p. 1506 - 1510

31
[ 4152-92-5 ]
[ 397870-23-4 ]

Reference： [1]Synlett,2001,p. 1506 - 1510

32
[ 4152-92-5 ]
[ 17300-02-6 ]

Reference： [1]Russian Journal of General Chemistry,2001,vol. 71,p. 817 - 818

33
[ 4152-92-5 ]
[ 198127-17-2 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8280 - 8281

34
[ 4152-92-5 ]
[2-(1-ethyl-2-aza-bicyclo[3.3.1]non-2-ylmethyl)-phenyl]-methanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8280 - 8281
[2]Journal of Organic Chemistry,1997,vol. 62,p. 8280 - 8281

35
[ 4152-92-5 ]
3-[2-(2-hydroxymethyl-benzylamino)-ethyl]-cyclohexanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8280 - 8281

36
[ 4152-92-5 ]
[2-(1-allyl-2-aza-bicyclo[3.3.1]non-2-ylmethyl)-phenyl]-methanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8280 - 8281

37
[ 4152-92-5 ]
[2-(1-benzyl-2-aza-bicyclo[3.3.1]non-2-ylmethyl)-phenyl]-methanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8280 - 8281

38
[ 14758-57-7 ]
[ 4152-92-5 ]

Reference： [1]Gazzetta Chimica Italiana,1966,vol. 96,p. 1671 - 1695

39
[ 91-13-4 ]
[ 4152-92-5 ]

Reference： [1]Gazzetta Chimica Italiana,1966,vol. 96,p. 1671 - 1695

40
[ 4152-92-5 ]
[ 39976-25-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1972,vol. 9,p. 1209 - 1214

41
[ 4152-92-5 ]
[ 39976-41-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1972,vol. 9,p. 1209 - 1214

42
[ 4152-92-5 ]
[ 39976-42-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1972,vol. 9,p. 1209 - 1214

43
[ 4152-92-5 ]
[ 39976-43-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1972,vol. 9,p. 1209 - 1214

44
[ 4152-92-5 ]
[ 86652-64-4 ]
[ 590-86-3 ]
C₄₂H₄₉N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 14(3/?,6R)-3-(2,3-Dihydro-1H-inden-2-yl)-1-[2-(hydroxymethyl)-phenyl]methyI}-6-(2- methylpropyl)-2,5-piperazinedione [2-(Aminomethyl)phenyl]methanol (3.509 g, 25.58 mmol) was dissolved in methanol (25ml) and 3-methylbutanal (2.75ml, 25.63 mmol) added followed by (2R)-2,3-dihydro- 1H-inden-2-yl([(1 ,1-dimethylethyl)oxy]carbonyl}amino)ethanoic acid (7.453 g, 25.58 mmol). The mixture was stirred for 15 minutes before 2-[(phenylmethyl)oxy]phenyl isocyanide (5.35 g, 25.58 mmol) was added. The mixture was stirred for 1.3 hours and then left to stand at room temperature over 7 nights before it was cooled in an ice / water bath. Then acetyl chloride (10.9 ml, 153.4 mmol) was added. Then the mixture was stirred in the cooling bath for a further 10 minutes before it was stirred at room temperature. After 4.25 hours the mixture was evaporated under reduced pressure to leave a dark brown foam. The foam was stirred in chloroform (50 ml) and saturated aqueous sodium bicarbonate solution (40 ml) for 60 minutes before it was diluted with chloroform (100 ml) and the phases separated. The aqueous phase was extracted with chloroform (3 * 50 ml). The combined organic phase was dried (MgSO4) and concentrated under reduced pressure to ca. 80 ml. The chloroform solution was treated with glacial acetic acid (2ml) and left to stand, at room temperature for five nights. Then the reaction mixture was washed with 2M hydrochloric acid (70 ml) diluted with chloroform (140 ml) and filtered. The filtered organic phase was washed with saturated aqueous sodium bicarbonate solution (70 ml). The organic phase was dried (MgSO4), evaporated under reduced pressure and dried in vacuo to leave a dark brown solid. The solid was loaded in dichloromethane onto a 33Og flash silica chromatography column (pre-eluted with 20% ethyl acetate in cyclohexane). The column was eluted with 20% to 100% ethyl acetate in cyclohexane to afford (3R,6f?)-3-(2,3-dihydro-1H-inden-2-yl)-1-[2- (hydroxymethyl)phenyl]methyl}-6-(2-methylpropyl)-2,5-piperazinedione (1.563 g) as a pale brown foam. LCMS (A) Rt = 3.17 minutes; m/z [M+H]+ = 407.

Reference： [1]Patent: WO2006/67462,2006,A1 .Location in patent: Page/Page column 51

45
[ 181227-48-5 ]
[ 1885-81-0 ]
[ 4152-92-5 ]
C₃₇H₄₆ClN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1(3R,6f?)-3-(2,3-Dihydro-1 H-inden-2-yl)-6-(1 -ethylpropyl)-1 -[2(hydroxymethyl)- benzyI]piperazine-2,5-dione [2-(Aminomethyl)phenyl]methanol (4.12g, 30 mmol) was dissolved in methanol (30ml) and 2-ethylbutanal (3.7ml, 30 mmol) added followed by (2R)-2,3-dihydro-1H-inden-2- yl([(1 ,1-dimethylethyl)oxy]carbonyl}amino)ethanoic acid (8.74g, 30 mmol). The mixture was stirred for 15 minutes before 4-chlorophenylisonitrile (4.13g, 30 mmol) was added. The mixture was stirred for 2.25 hours and then left to stand at room temperature overnight (16.3 hours) before it was cooled in an ice / water bath. Then acetyl chloride (12.75ml, 179.5 mmol) was added dropwise, keeping the reaction temperature below 200C. Then the mixture was stirred in the cooling bath for a further 10 minutes before it was stirred at room temperature. After 5 hours the mixture was evaporated under reduced pressure to leave a dark brown gum. The gum was stirred in chloroform (75ml) and saturated aqueous sodium bicarbonate solution (75ml) for 20 minutes before it was diluted with chloroform (75ml) and the phases separated. The aqueous phase was extracted with chloroform (3 * 75ml). The combined organic phase was dried (MgSO4) and concentrated under reduced pressure to ca. 75ml. The chloroform solution was treated with glacial acetic acid (3ml) and left to stand, at room temperature over the weekend. Then the reaction mixture was washed with 2M hydrochloric acid (75ml), followed by saturated aqueous sodium bicarbonate solution (75ml). The organic phase was dried (MgSO4) and evaporated under reduced pressure and dried to leave a brown foam. The foam was loaded in dichloromethane onto a 33Og flash silica chromatography column (pre-eluted with 20% ethyl acetate in cyclohexane). The column was eluted with 20% to 100% ethyl acetate in cyclohexane to afford (3f?,6R)-3-(2,3-dihydro-1H-inden-2- yl)-6-(1-ethylpropyl)-1-[2-(hydroxymethyl)benzyl]piperazine-2,5-dione (4.12g) as a pale brown solid. HPLC (A) Rt = 3.26 minutes; m/z [M+H]+ = 421. EPO <DP n="69"/>1H NMR (CDCI3) delta 7.37 (m, 1 H), 7.30 (m, 2H), 7.21 (m, 5H), 6.84 (br d,1 H), 5.45 (d, 1 H), 4.74 and 4.63 (d, 2H), 4.16 (d, 1 H), 4.08 (dd, 1 H), 4.04 (d, 1 H), 3.15 (m, 3H), 2.92 (m, 1H), 2.78 (m, 2H), 1.76 (m, 1 H), 1.62 (m, 3H), 1.31 (m, 1 H), 0.92 (m, 6H).

Reference： [1]Patent: WO2006/67462,2006,A1 .Location in patent: Page/Page column 67-68

46
[ 4152-92-5 ]
[ 168761-51-1 ]
[ 182963-62-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine; In tetrahydrofuran;	REFERENCE EXAMPLE 4 7-Ethylamino-4-[2-(hydroxymethyl)benzylamino]-6-nitroquinazoline 4-Chloro-7-ethylamino-6-nitroquinazoline (11.58 g, 45.9 mmol) obtained in Reference Example 2 was suspended in tetrahydrofuran (400 ml), and <strong>[4152-92-5]2-(hydroxymethyl)benzylamine</strong> (7.50 g, 54.7 mmol) obtained in Reference Example 3 and triethylamine (30 ml) were added thereto, followed by stirring at room temperature for one night. After the reaction, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution of chloroform--chloroform/methanol=100) to give the title compound (10.60 g, 65%). 1 H-NMR (CDCl3) delta(ppm): 1.39(3H, t, J=7.1 Hz), 3.38(2H, q, J=7.1 Hz), 4.75(2H, s), 4.85(2H, s), 6.89(1H, s), 7.25-7.30(2H, m), 7.41-7.44(2H, m), 7.69(1H, s), 8.36(1H, s), 8.95(1H, br), 9.27(1H, s).

Reference： [1]Patent: US5698560,1997,A

Yield	Reaction Conditions	Operation in experiment
		N-[methyl(2-((t-butyldimethylsilyloxy)methyl)phenyl)]-N-[(N-carbo-t-butoxy)piperidin-4-yl]amine A solution of methyl-2-cyanobenzoate (10 g, 62.11 mmol) in ethyl ether (300 mL) was added dropwise to a slurry of lithium aluminum hydride in ethyl ether (200 mL). After the addition was complete, more ether was added (200 mL) and the mixture heated at reflux for 2 h. The cooled reaction mixture was quenched by careful addition of succesive amounts of water (7.1 mL), 1N sodium hydroxide solution (7.1 mL) and water (21.3 mL). The reaction was filtered and evaporated to give 6.96 g (50.8 mmol) of 2-(aminomethyl)benzyl alcohol. This material was carried on without further purification. The material from above was dissolved in tetrahydrofuran (140 mL) and cooled to 0 C.

48
[ 4152-92-5 ]
[ 496-12-8 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 312 - 315

49
[ 1253889-37-0 ]
[ 4152-92-5 ]
[ 1253889-43-8 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 6633 - 6637
[2]Chemistry - A European Journal,2012,vol. 18,p. 1383 - 1400

50
[ 4152-92-5 ]
[ 74785-02-7 ]
[ 1258652-35-5 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 17366 - 17369

51
[ 24424-99-5 ]
[ 4152-92-5 ]
[ 1333114-86-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	In methanol; dichloromethane; at 20℃; for 24h;	To a solution of 8a (4 g, 29.2 mmol) in DCM (20 mL) and MeOH (10 mL) was added Boc20 (6.4 g, 29.2 mmol). The reaction mixture was stirred at rt for 24 h and concentrated under reduce pressure. The residue was purified by CC on silica gel, eluting with RhoEpsilonXi/EpsilonAlpha = 10:1 to 5:1 to give 8b (3.2 g, 46% yield) as a white solid.

Reference： [1]Patent: WO2011/107248,2011,A1 .Location in patent: Page/Page column 47

52
[ 4152-92-5 ]
[ 1333114-87-6 ]

Reference： [1]Patent: WO2011/107248,2011,A1

53
[ 4152-92-5 ]
[ 1333114-88-7 ]

Reference： [1]Patent: WO2011/107248,2011,A1

54
[ 4152-92-5 ]
[ 1333114-89-8 ]

Reference： [1]Patent: WO2011/107248,2011,A1

55
[ 4152-92-5 ]
[ 1333114-90-1 ]

Reference： [1]Patent: WO2011/107248,2011,A1

56
[ 4152-92-5 ]
[ 1333114-91-2 ]

Reference： [1]Patent: WO2011/107248,2011,A1

57
[ 4152-92-5 ]
[ 1333114-92-3 ]

Reference： [1]Patent: WO2011/107248,2011,A1

58
[ 4152-92-5 ]
[ 616-38-6 ]
[ 18913-40-1 ]

Reference： [1]Green Chemistry,2012,vol. 14,p. 58 - 61

59
[ 1253889-37-0 ]
[ 4152-92-5 ]
N⁽¹⁾-(4-butylphenyl)-N⁽²⁾-(2-(((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)methyl)benzyl)phthalamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1383 - 1400

60
[ 4152-92-5 ]
[ 98-88-4 ]
N-(2-(((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)methyl)benzyl)benzamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10368 - 10381

61
[ 4152-92-5 ]
[ 98-88-4 ]
[ 1402088-39-4 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 10368 - 10381

62
[ 4152-92-5 ]
[ 98-59-9 ]
[ 127459-01-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11524 - 11527,4

63
[ 4152-92-5 ]
[ 98-59-9 ]
N-(2-(hydroxymethyl)benzyl)-4-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11524 - 11527,4
[2]Organic Letters,2016,vol. 18,p. 642 - 645

64
[ 4152-92-5 ]
[ 124-63-0 ]
[ 75-36-5 ]
[ 1417893-40-3 ]

Yield	Reaction Conditions	Operation in experiment
		[00177] Compound 24: An ice-cold pyridine solution (10 mL) of compound 23 (1 mmol) is treated successively, in a dropwise fashion with acetyl choride (1 mmol), then after 5 min with MsCl (1.1 mmol). The solution is warmed to room temperature then the solvent is removed. The residue is dissolved in EtOAc, washed with water, dried (MgS04), filtered and reduced in vacuo. Purification by column chromatography affords pure compound 24.
		An ice-cold pyridine solution (10 mL) of compound 23 (1 mmol) is treated successively, in a dropwise fashion with acetyl chloride (1 mmol), then after 5 min with MsCl (1.1 mmol). The solution is warmed to room temperature then the solvent is removed. The residue is dissolved in EtOAc, washed with water, dried (MgS04), filtered and concentrated in vacuo. Purification by column chromatography affords pure compound 24.

Reference： [1]Patent: WO2013/12758,2013,A1 .Location in patent: Paragraph 00177
[2]Patent: WO2014/12081,2014,A2 .Location in patent: Paragraph 0017; 0035

65
[ 4152-92-5 ]
[ 32372-82-0 ]

Reference： [1]Organic Syntheses,2013,vol. 90,p. 251 - 260

66
[ 4152-92-5 ]
[ 38379-25-8 ]

Reference： [1]Organic Syntheses,2013,vol. 90,p. 251 - 260

67
[ 934554-40-2 ]
[ 4152-92-5 ]
{2-([3,4-dihydrospiro(1-benzopyran-2,1'-cyclobutane)-4-yl]amino}methyl)phenyl}methanol [ No CAS ]

Reference： [1]Synthesis,2014,vol. 46,p. 1765 - 1772

68
[ 934554-40-2 ]
[ 4152-92-5 ]
C₂₀H₂₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) isopropylate; N-trimethylsilyl-pyrrolidin-2-one; at 70℃; for 6h;Sealed tube;	General procedure: Step i: Ketone 1 (1 mmol), primary amine 2 (1 mmol), and a mixture of Ti(Oi-Pr)4 (3.1 mg, 1.1 mol%) in 1-(trimethylsilyl)-2-pyrrolidinone (393 mg, 2.5 mmol) were heated at 70C with shaking in a sealed vial for 6 h. Step ii: After cooling down to r.t., EtOH (2 mL) was added to the solution and it was shaken until homogenization followed by the addition of NaBH4 (68 mg, 1.8 mmol). The resulting heterogeneous mixture was left staying overnight at r.t. Then, H2O (2 mL) was added and the mixture was sonicated for 2 h at r.t. to decompose the excess of NaBH4. The product was extracted with CHCl3 (3 mL), and the organic phase was washed with H2O (3 × 7 mL), dried (Na2SO4), and evaporated to give the respective secondary amine 3. Samples with purity below 95% as determined by LC-MS or 1H NMR spectroscopy were further purified by column chromatography (SiO2,eluent A: CHCl3, eluent B: i-PrOH, a linear gradient from 0% eluent B to 100% eluent B was used).

Reference： [1]Synthesis,2014,vol. 46,p. 1765 - 1772

69
[ 4152-92-5 ]
N-(but-3-en-1-yl)-N-(2-(hydroxymethyl)benzyl)-4-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 642 - 645

70
[ 4152-92-5 ]
3-Propyl-4-tosyl-1,3,4,5-tetrahydrobenzo[e][2,4]oxazepine [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 642 - 645

71
[ 4152-92-5 ]
[ 1055972-12-7 ]

Reference： [1]Patent: CN104031048,2016,B

72
[ 4152-92-5 ]
[ 948903-70-6 ]

Reference： [1]Patent: CN104031048,2016,B

73
[ 4152-92-5 ]
1-(O-6-[2-(aminomethyl)benzyl]guanine)-3-(2-chloroethyl)urea [ No CAS ]

Reference： [1]Patent: CN104031048,2016,B

74
[ 4152-92-5 ]
1-(O-6-[2-(aminomethyl)benzyl]guanine)-3-(2-chloroethyl)-1-nitrourea [ No CAS ]

Reference： [1]Patent: CN104031048,2016,B

75
[ 383-63-1 ]
[ 4152-92-5 ]
[ 948903-65-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine; In methanol; at 25℃; for 2h;Inert atmosphere;	A solution of 1.7 g of <strong>[4152-92-5]2-(aminomethyl)benzyl alcohol</strong> (12. 4 mmol) and 1.76 mL of triethylamine (12. 4 mmol) was dissolved in 20 mL anhydrous methanol, 1.96 mL of ethyl trifluoroacetate (16.4 mmol) was added dropwise under argon and the reaction was stirred at 25 C for 2 hours. After the reaction, ethyl acetate (30 mL) and water (30 mL) were added to the extract. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate overnight, and the solvent was removed in vacuo to give 2-[(trifluoroacetamido)methyl]benzyl alcohol. The crude product was purified by silica gel column chromatography eluting with ethyl acetate / cyclohexane (1: 2, v / v) to give 2-[(trifluoroacetamido)methyl]benzyl alcohol (2.0 g, 8.6 mmol), 69% yield.

Reference： [1]Patent: CN104031048,2016,B .Location in patent: Paragraph 0093; 0094
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 13351 - 13355
Angew. Chem.,2017,vol. 129,p. 13536 - 13540,5

76
[ 4152-92-5 ]
2,2,2-trifluoro-N-(2-(hydroxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)acetamide [ No CAS ]
C₁₆H₂₁BF₃NO₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 13351 - 13355
Angew. Chem.,2017,vol. 129,p. 13536 - 13540,5

77
[ 4152-92-5 ]
[ 98-58-8 ]
C₁₄H₁₄BrNO₃S [ No CAS ]