Isopropanol → (S)-2-amino-1-(3-chlorophenyl)ethanol

HRID 561902Notes

Reaction equation

HRID 561902 reaction equation
[N:1]([CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[OH:6])=[N+]=[N-].[BH4-].[Na+].C(O)(C)C>CO>[NH2:1][CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[OH:6]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 59761679(1S)-2-azido-1-(3-chlorophenyl)ethan-1-ol

Product 1

HCID 9855591(S)-2-amino-1-(3-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-2-Azido-1-(3-chlorophenyl)-ethanol (5.14 g, 0.026 mol), NaBH4 (1.97 g, 0.052 mol) and isopropyl alcohol (100 mL) was stirred at 80° C. for 24 h. The solvent was evaporated, the residue was separated on SiO2 (15 g) CHCl3-MeOH (0 to 30%). Colorless oil, 3.70 g (0.021 mol, 83%). The material was reacted with Boc2O in dichloromethane and NEt3 and analyzed by chiral SFC using a CHIRALPAK AD-H column, 30% MeOH and determined to be 91% ee.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was separated on SiO2 (15 g) CHCl3-MeOH (0 to 30%)
  3. customThe material was reacted with Boc2O in dichloromethane and NEt3

Sources & evidence

ORD record
ord-580d4fe2ffbe48f3919cf5dd0fa76f9c
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

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