Hydrochloric Acid → (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine

Participants

Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine (11.11 g) in methanol (110 ml) was added conc. hydrochloric acid (7.32 ml) at ambient temperature with stirring and the solution was stirred at the same temperature for 2 hours. To a reaction solution was added 28% sodium methoxide-methanol solution (16.89 ml) under ice-cooling with stirring and the resulting insoluble material was filtered off. The filtrate was evaporated in vacuo to give a residue. To the residue was added chloroform. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to give crude (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine (9.19 g).

Provenance & Evidence