Dimethylformamide → (2R,4R)-1-allyloxy-carbonyl-4-(t-butyldimethylsilyloxy)-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

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Reaction Conditions

Reaction Steps

A mixture of (2R,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(2-methanesulfonyloxyethyl)pyrrolidine (10.0 g) and 1,2,4-triazole sodium salt (2.45 g) in dimethylformamide (50 ml) was stirred at 60° C. for 3.5 hours. After cooling to room temperature, the mixture was quenched by the addition of water (100 ml) and extracted with a mixture of hexane and ethyl acetate (2:1, 50 ml×4). The combined extract was washed with water (400 ml), brine (100 ml) and dried over magnesium sulfate. Evaporation of the solvent gave (2R,4R)-1-allyloxy-carbonyl-4-(t-butyldimethylsilyloxy)-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine (8.82 g) as a light brown paste.

Provenance & Evidence