Sodium borohydride → tert-butyl((1S)-2-hydroxy-1-phenylpropyl)carbamate

HRID 588117Notes

Reaction equation

HRID 588117 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9](=[O:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]([OH:11])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90251117(S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate

Product 1

HCID 117997689tert-butyl((1S)-2-hydroxy-1-phenylpropyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., to a solution of ((S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate (0.7 g, 2.8 mmol) in MeOH (10 mL) was added NaBH4 (0.1 g, 2.8 mmol) and the contents were stirred at ambient temperature. After 30 min, the reaction mixture was quenched carefully with ice cold H2O (10 mL), and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated to afford tert-butyl((1S)-2-hydroxy-1-phenylpropyl)carbamate. The product thus obtained was pure and taken directly for the next step without further purification. MS: [M+H-Boc]+ m/z 152.

Workup

  1. customthe reaction mixture was quenched carefully with ice cold H2O (10 mL)
  2. extractionthe organic contents were extracted with EtOAc (3×25 mL)
  3. washThe combined organic extracts were washed with brine (1×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-664b902a0fbc4f7a8a436d5c21c73e5b
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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