Triethylamine → (S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone

HRID 1534560Notes

Reaction equation

HRID 1534560 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]#[CH:9])[C:4](=[O:10])[CH2:3]1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[CH3:15][C:14]([Si:11]([CH3:13])([CH3:12])[O:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]#[CH:9])[C:4](=[O:10])[CH2:3]1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 15046658(S)-4-hydroxy-1-(2-propynyl)-2-pyrrolidinone

Product 1

HCID 15086816(S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinoneYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 25 g of (S)-4-hydroxy-1-(2-propynyl)-2-pyrrolidinone, 39.8 g of t-butyldimethylsilyl chloride and 38.5 ml of triethylamine in 200 ml of dichloromethane was stirred under argon overnight. The mixture was washed with 300 ml of water, dried and evaporated. The residual oil was purified by chromatgraphy, (silica gel) giving 42.7 g of (S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone.

Workup

  1. washThe mixture was washed with 300 ml of water
  2. customdried
  3. customevaporated
  4. customThe residual oil was purified by chromatgraphy, (silica gel)

Sources & evidence

ORD record
ord-ba1f9651c9cb47aeb78ee02b8044845c
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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