162118-01-6

Basic information

• Product Name: (S)-DIPHENYLALANINOL
• Synonyms: (S)-DIPHENYLALANINOL;(S)-2-AMino-3,3-diphenylpropan-1-ol;Benzenepropanol, b-aMino-g-phenyl-, (bS)-
• CAS NO: 162118-01-6
• Molecular Formula: C₁₅H₁₇NO
• Molecular Weight: 227.3
• Mol File: 162118-01-6.mol

Chemical Properties

• Boiling Point: 410.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.113±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 12.62±0.10(Predicted)
• CAS DataBase Reference: (S)-DIPHENYLALANINOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-DIPHENYLALANINOL(162118-01-6)
• EPA Substance Registry System: (S)-DIPHENYLALANINOL(162118-01-6)

Safety Data

• Hazardous Substances Data: 162118-01-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
(S)-DIPHENYLALANINOL is used as a catalyst in asymmetric syntheses for its ability to induce chirality in chemical reactions, leading to the production of enantiomerically pure compounds.
Used in Pharmaceutical Industry:
(S)-DIPHENYLALANINOL is used as a building block in the production of various pharmaceutical compounds, contributing to the development of new drugs with improved efficacy and selectivity.
Used in Fragrance Industry:
(S)-DIPHENYLALANINOL is used as a precursor in the synthesis of various flavors and fragrances due to its aromatic properties, enhancing the sensory experience of consumer products.
Used in Chiral Auxiliary Applications:
(S)-DIPHENYLALANINOL is used as a chiral auxiliary in asymmetric synthesis processes, facilitating the production of enantiomerically pure compounds with high selectivity and yield.

Synthetic route

tert-butyl N-[(1S)-1-(hydroxymethyl)-2,2-diphenylethyl]carbamate (155836-47-8) → (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃; for 48h; Hydrolysis;	100%
With trifluoroacetic acid for 1h; Cooling with ice;

C25H22N4O3 → (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃;

3-(1-imidazolyl)benzonitrile (25699-85-8) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → C25H21N3O

Conditions	Yield
With zinc(II) trifluoroacetate In chlorobenzene at 130℃; for 48h; Inert atmosphere; Schlenk technique;	93%

diethyl malonoimidate dihydrochloride (10344-69-1) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → bis((S)-4-benzhydryl-4,5-dihydrooxazol-2-yl)methane

Conditions	Yield
In dichloromethane at 40℃; for 8h;	75%

quinoline-2-carbonitrile (1436-43-7) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-2-(quinolin-2-yl)-4,5-dihydrooxazole

Conditions	Yield
Stage #1: quinoline-2-carbonitrile With sodium methylate In methanol at 20℃; Stage #2: (S)-2-amino-3,3-diphenyl-1-propanol With toluene-4-sulfonic acid In toluene at 80℃;	64%

ethyl 5-(benzyloxy)-6-((2-methoxyethyl)carbamoyl)-4-oxo-4H-pyran-3-carboxylate (1246616-94-3) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → ethyl (S)-5-(benzyloxy)-1-(3-hydroxy-1,1-diphenylpropan-2-yl)-6-((2-methoxyethyl)carbamoyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (1370248-11-5)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 0.5h;	52%
With triethylamine In toluene at 90℃; for 1h;	9.12 g

pyridine-2,6-dinitrile (2893-33-6) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → 2,6-bis((S)-4-benzhydryl-4,5-dihydrooxazol-2-yl)pyridine

Conditions	Yield
With zinc trifluoromethanesulfonate In toluene for 48h; Reflux;	35%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → tert-butyl N-[(1S)-1-(hydroxymethyl)-2,2-diphenylethyl]carbamate (155836-47-8)

Conditions	Yield
In dichloromethane

5-chlorothien-2-ylsulfonyl chloride (2766-74-7) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → C19H18ClNO3S2 (1132652-97-1)

Conditions	Yield
With triethylamine In tetrahydrofuran

diphenylamine-2,2'-dicarbonyl chloride (32621-46-8) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → C44H41N3O4

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → ethyl (S)-4-benzhydryl-9-(benzyloxy)-2-(2-methoxyethyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate (1370248-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / toluene / 1 h / 90 °C 2: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-(benzyloxy)-2-(2-methoxyethyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid (1370248-13-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / toluene / 1 h / 90 °C 2: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3: sodium hydroxide; water / ethanol / 1.17 h / 20 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-hydroxy-2-(2-methoxyethyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid (1370237-33-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / toluene / 1 h / 90 °C 2: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4: palladium 10% on activated carbon; hydrogen / methanol / 1 h View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → C32H32N2O5 (1370248-22-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.33 h / 0 °C 4.2: 2.5 h / 0 - 20 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → C25H26N2O5 (1370237-80-1)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.33 h / 0 °C 4.2: 2.5 h / 0 - 20 °C 5.1: trifluoroacetic acid / 1 h / 20 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-(benzyloxy)-N-methoxy-2-(2-methoxyethyl)-N-methyl-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxamide (1370248-38-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Cooling with ice 4.2: 1 h / 20 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-7-acetyl-4-benzhydryl-9-(benzyloxy)-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (1370248-39-7)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Cooling with ice 4.2: 1 h / 20 °C 5.1: tetrahydrofuran / 0.5 h / -78 - -50 °C / Inert atmosphere View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → C33H32N2O6 (1370248-40-0)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Cooling with ice 4.2: 1 h / 20 °C 5.1: tetrahydrofuran / 0.5 h / -78 - -50 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-(benzyloxy)-7-hydroxy-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (1370248-41-1)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Cooling with ice 4.2: 1 h / 20 °C 5.1: tetrahydrofuran / 0.5 h / -78 - -50 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 7.1: ethanol / 4 h / Reflux View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-(benzyloxy)-7-methoxy-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (1370248-42-2)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Cooling with ice 4.2: 1 h / 20 °C 5.1: tetrahydrofuran / 0.5 h / -78 - -50 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 7.1: ethanol / 4 h / Reflux 8.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / Cooling with ice 8.2: 1.5 h / 20 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-hydroxy-7-methoxy-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (1370237-92-5)

Conditions

Yield

Multi-step reaction with 9 steps 1.1: triethylamine / toluene / 1 h / 90 °C 2.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3.1: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4.1: chloroformic acid ethyl ester; triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C / Cooling with ice 4.2: 1 h / 20 °C 5.1: tetrahydrofuran / 0.5 h / -78 - -50 °C / Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 7.1: ethanol / 4 h / Reflux 8.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / Cooling with ice 8.2: 1.5 h / 20 °C 9.1: trifluoroacetic acid / 0.5 h / 20 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-(benzyloxy)-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (1370248-43-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / toluene / 1 h / 90 °C 2: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4: diphenylether / 1 h / 245 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-9-(benzyloxy)-7-bromo-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (1370248-44-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: triethylamine / toluene / 1 h / 90 °C 2: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4: diphenylether / 1 h / 245 °C 5: N-Bromosuccinimide / dichloromethane / 1 h / Reflux View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → C24H23BrN2O4 (1370237-93-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: triethylamine / toluene / 1 h / 90 °C 2: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 20 h / 20 °C / Cooling with ice 3: sodium hydroxide; water / ethanol / 1.17 h / 20 °C 4: diphenylether / 1 h / 245 °C 5: N-Bromosuccinimide / dichloromethane / 1 h / Reflux 6: trifluoroacetic acid / 0.83 h / 20 °C View Scheme

2,2-dimethylpent-4-enoic acid (16386-93-9) + (S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (S)-4-benzhydryl-2-(2-methylpent-4-en-2-yl)-4,5-dihydrooxazole

Conditions	Yield
Stage #1: 2,2-dimethylpent-4-enoic acid; (S)-2-amino-3,3-diphenyl-1-propanol With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Stage #2: With dmap; methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃;

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (4S,4'S)-2,2'-(pentane-3,3-diyl)bis(4-benzhydryl-4,5-dihydrooxazole)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dichloromethane / 8 h / 40 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C 2.2: 8 h / 60 °C View Scheme

(S)-2-amino-3,3-diphenyl-1-propanol (162118-01-6) → (4S,4'S)-2,2'-(cyclopentane-1,1-diyl)bis(4-benzhydryl-4,5-dihydrooxazole)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dichloromethane / 8 h / 40 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C 2.2: 8 h / 60 °C View Scheme

Upstream product

• 155836-47-8 tert-butyl N-[(1S)-1-(hydroxymethyl)-2,2-diphenylethyl]carbamate 

Downstream Products

• 1132652-97-1 C₁₉H₁₈ClNO₃S₂ 
• 1370248-11-5 ethyl (S)-5-(benzyloxy)-1-(3-hydroxy-1,1-diphenylpropan-2-yl)-6-((2-methoxyethyl)carbamoyl)-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1370237-93-6 C₂₄H₂₃BrN₂O₄ 
• 1370248-44-4 (S)-4-benzhydryl-9-(benzyloxy)-7-bromo-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione 
• 1370248-43-3 (S)-4-benzhydryl-9-(benzyloxy)-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione 
• 1370237-92-5 (S)-4-benzhydryl-9-hydroxy-7-methoxy-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione 
• 1370248-42-2 (S)-4-benzhydryl-9-(benzyloxy)-7-methoxy-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione 
• 1370248-41-1 (S)-4-benzhydryl-9-(benzyloxy)-7-hydroxy-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione 
• 1370248-40-0 C₃₃H₃₂N₂O₆ 
• 1370248-39-7 (S)-7-acetyl-4-benzhydryl-9-(benzyloxy)-2-(2-methoxyethyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione 
• 1370248-38-6 (S)-4-benzhydryl-9-(benzyloxy)-N-methoxy-2-(2-methoxyethyl)-N-methyl-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxamide 
• 1370237-80-1 C₂₅H₂₆N₂O₅ 
• 1370248-22-8 C₃₂H₃₂N₂O₅ 
• 1370237-33-4 (S)-4-benzhydryl-9-hydroxy-2-(2-methoxyethyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid 

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