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

HRID 2107994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2107994
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 15086816(S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinoneAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 chromatography, (silica gel) giving 42.7 g of (S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f92668d1f7b343f885f0441495249056
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04937235

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