Water → (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-{2-(5-formylimidazol-1-yl)ethyl}pyrrolidine

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Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-{2-(methanesulfonyloxy)ethyl}pyrrolidine (38.8 g) in N,N-dimethylformamide (380 ml) were added 4-formylimidazole (13.0 g) and potassium t-butoxide (15.2 g) and the mixture was stirred at 50°-60° C. for 2 hours. The reaction mixture was poured into water (600 ml) and extracted three times with ethyl acetate (400 ml). The extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (750 g) eluting with a mixture of 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-4-methanesulfonyloxy-2-{2-(5-formylimidazol-1-yl)ethyl}pyrrolidine (14.2 g).

Provenance & Evidence