Hydrochloric Acid → HCID 53646177, compound

Participants

Reaction Steps

A solution of (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[2-(1-methylimidazol-2-yl)vinyl]pyrrolidine (5.70 g), conc. hydrochloric acid (2.34 ml) and 10% palladium on carbon (50% wet) (3.0 g) in methanol (120 ml) was stirred under atmospheric pressure of hydrogen at ambient temperature for 4 hours. The catalyst was filtered off and the filtrate was concentrated in vacuo. The resulting residue was dissolved in a mixture of tetrahydrofuran (60 ml) and water (60 ml). To solution was added dropwise a solution of allyloxycarbonyl chloride (1.94 ml) in tetrahydrofuran (5 ml) keeping the pH 8-10 with 4N sodium hydroxide under ice-cooling and then the mixture was stirred at the same temperature for 1 hour. The reaction mixture was concentrated in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 ml) and then the solution was washed twice with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2R,4R)-1-allyloxycarbonyl-2-[2-(1-methylimidazol-2-yl)ethyl]-4-methanesulfonyloxypyrrolidine (5.69 g).

Provenance & Evidence