1-Chloroethyl chloroformate → 3-((Tert-butyldiphenylsilyl)oxy)azetidine

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 1-benzhydryl-3-(tert-butyl-diphenyl-silanyloxy)-azetidine (162a) (4.0 g, 8.4 mmol) in DCE (60 ml) at room temperature is treated with 1-chloroethylchloroformate (1.2 ml, 10.9 mmol) and the reaction mixture is heated to 80° C. After 2 hours, the solvent is removed in vacuo and the residue is dissolved in methanol (60 ml) and heated to reflux. After 1 h the reaction mixture is poured into water (250 ml), acidified with hydrochloric acid (1M solution) and washed with EtOAc (3×75 ml). The aqueous solution is basified with saturated sodium bicarbonate solution and extracted with EtOAc (3×75 ml). The combined organic layers are washed with water (2×50 ml), brine (50 ml), dried over MgSO4. The solvent is removed in vacuo to yield the titled compound.

Provenance & Evidence