Imidazole → HCID 15117255, compound

Participants

Reaction Steps

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (60 g) and imidazole (12.9 g) in dichloromethane (300 ml) was added dropwise a solution of tert-butyldimethylsilyl chloride (31.4 g) in dichloromethane at 0° C. over a 30-minute period. After one hour, the reaction mixture was poured into a mixture of ethyl acetate (1 l), water (400 ml) and saturated aqueous sodium chloride (200 ml). The organic layer was separated, washed in turn with water and brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (1.2 l) eluting with a mixture of hexane and ethyl acetate (1:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-(tert-butyldimethylsilyloxy)methyl-4-methanesulfonyloxypyrrolidine (71 g).

Provenance & Evidence