Sodium borohydride → Tert-butyl [1-hydroxy-3-(methylsulfanyl)propan-2-yl]carbamate

HRID 1504830Notes

Reaction equation

HRID 1504830 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13](OC(OCC)=O)=[O:14])[CH2:10][S:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Cl-].[NH4+]>[OH:14][CH2:13][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][S:11][CH3:12]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86731709ethoxycarbonyl N-(tert-butoxycarbonyl)-S-methylcysteinate

Product 1

HCID 15192845Tert-butyl [1-hydroxy-3-(methylsulfanyl)propan-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of ethoxycarbonyl N-(tert-butoxycarbonyl)-S-methylcysteinate (18.5 g, 60.3 mmol) in methanol (300 mL) was added sodium borohydride (9.12 g, 0.240 mol) at 0° C., and then the reaction mixture was allowed to warm to ambient temperature. After 2 hours, the reaction mixture was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give tert-butyl [1-hydroxy-3-(methylsulfanyl)propan-2-yl]carbamate which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-546ac8b87fa042b7b8e904774f99b1de
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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