Ammonia → (S)-2-(tert-butyldimethylsilyloxy)-4-hydroxybutanamide

HRID 1917502Notes

Reaction equation

HRID 1917502 reaction equation
[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][O:11][C:10]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:15]>CO>[Si:1]([O:8][C@@H:9]([CH2:13][CH2:12][OH:11])[C:10]([NH2:15])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 50462413-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one

Product 1

HCID 57999203(S)-2-(tert-butyldimethylsilyloxy)-4-hydroxybutanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one (11 g, 49 mmol) in methanol was added 7 N ammonia in methanol (20 mL, 140 mmol). The reaction was stirred in a sealed tube for 2 days. The solvent was removed in vacuo to yield (S)-2-(tert-butyldimethylsilyloxy)-4-hydroxybutanamide (4.85 g, 20.8 mmol) as a white solid. [M+H] calc'd for C10H23NO3Si, 234; found, 234.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-67fdef132c814f3ba814d75be9d4cc93
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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