Hydrochloric Acid → (S)-4-Hydroxy-1-[4-(1-pyrrolidinyl)2-butynyl]-2-pyrrolidinone

Reaktionsgleichung

CC([Si](C)(C)[O:6][C@@H:7]1[CH2:11][N:10]([CH2:12][C:13]#[C:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9](=[O:21])[CH2:8]1)(C)C.Cl.[OH-].[K+]>>[OH:6][C@@H:7]1[CH2:11][N:10]([CH2:12][C:13]#[C:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9](=[O:21])[CH2:8]1

Komponenten

Edukt 3

HCID 313Hydrochloric Acid

HCID 14797Potassium Hydroxide

HCID 15086817(S)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Produkt 1

HCID 15046677(S)-4-Hydroxy-1-[4-(1-pyrrolidinyl)2-butynyl]-2-pyrrolidinoneAusbeute 8,4 %

Versuchsvorschrift

A mixture of 7.2 g of (S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone and 75 ml of 1N methanolic hydrochloric acid was stirred for 1 hour, then cooled to 0° C. and basified to pH 8 with methanolic potassium hydroxide. The mixture was filtered and the filtrate evaporated. The residue was reevaporated from dichloromethane. The residual oil was purified by chromatography (alumina), giving 0.4 g of the desired product as a yellow oil, [α]D26 =-12° (dichloromethane).