Water → HCID 15086767, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 11.5 g of potassium tert-butoxide in 300 ml of dimethylformamide was cooled to -20° C. An 18 g portion of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]-oxy]-2-pyrrolidinone was added and the mixture stirred at -20° C. for 30 minutes. A 12 ml portion of 80% propargyl bromide in toluene was added and the reaction was allowed to warm to room temperature and was stirred for 1 hour. Water was added and the mixture was extracted with 5×100 ml of ether and 3×100 ml of dichloromethane. The extracts were combined, backwashed with water, dried and concentrated in vacuo, giving 15.8 g of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone [α]D260 =-44° (dichloromethane); mp 35°-36° C.

Provenance & Evidence