Water → (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(methanesulfonyloxy)pyrrolidine

Participants

Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine (9.19 g) in dichloromethane (92 ml) were dropwise added triethylamine (5.79 ml) and methanesulfonyl chloride (3.22 ml) under ice cooling with stirring, and the solution was stirred at the same temperature for 1 hour. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of chloroform and methanol (9:1, V/V) to give (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(methanesulfonyloxy)pyrrolidine (4.24 g).

Provenance & Evidence