Water → HCID 18652161, compound

Participants

Reaction Steps

To a solution of (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-(imidazo[1,2-b]pyrazol-1-yl)methylpyrrolidine (3.16 g) in a mixture of ethyl acetate (60 ml) and triethylamine (2.27 ml) was dropwise added a solution of methanesulfonyl chloride (1.18 ml) in ethyl acetate (5 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added water (50 ml) with stirring and the organic layer was separated. The organic layer was washed in turn with saturated aqueous sodium chloride, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (60 g) eluting with a mixture of dichloromethane and acetone (2:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl -2-(imidazo[1,2-b]pyrazol-1-yl)methyl-4-methanesulfonyloxypyrrolidine (3.06 g).

Provenance & Evidence