Ethyl Acetate → (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(t-butyldimethylsilyloxy) pyrrolidine

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(2-methanesulfonyloxyethyl) pyrrolidine (37.6 g) and ammonium chloride (5.84 g) in dimethylformamide (185 ml) was added portionwise sodium azide (7.1 g) at ambient temperature. The mixture was stirred at 70° C. for 3 hours, and poured into a mixture of ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed twice with water and once with brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(t-butyl-dimethylsilyloxy) pyrrolidine (29.7 g).

Provenance & Evidence