Triethylamine → (S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

Participants

Reaction Steps

A mixture of 14 g of (S)-3-hydroxy-2-pyrrolidinone, 45 g of tert-butyldimethylsilyl chloride, 50 ml of triethylamine and 500 ml of dichloromethane was stirred overnight. The solution was washed four times with water, once with brine, dried and concentrated in vacuo. The residue was dissolved in 500 ml of methanol, refluxed overnight and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving 21.5 g of (S)-3-[[(1,1-dimethlethyl)dimethylsilyl]oxy]-2-pyrrolidinone; [α]D26° =-52° (dichloromethane); mp 48°-49° C.

Provenance & Evidence