Hydrochloric Acid → (2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-[{3-(ethoxycarbonyl)-2-propenyl}oxymethyl]-4-methanesulfonyloxypyrrolidine (10 g) in tetrahydrofuran (120 ml) was added dropwise 1.0 M solution of diisobutylaluminum hydride in toluene (56.6 ml) at -40° C. and the mixture was allowed to warm to 0° C. and stirred for 10 hours at the same temperature. The reaction mixture was added dropwise 1N hydrochloric acid (50 ml), and the resulting precipitate was filtered off. The filtrate was dissolved in a mixture of ethyl acetate (200 ml) and water (100 ml). The organic layer was separated, washed with brine (100 ml), dried over magnesium sulfate and treated with active carbon. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:4 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-(4-hydroxy-2-butenyl)oxymethyl-4-methanesulfonyloxypyrrolidine (5.07 g).

Provenance & Evidence