Imidazole → (S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate

Participants

Reaction Steps

(S)-Benzyl-3-hydroxyglutaramate (49.5 g) was dissolved in anhydrous dimethylformamide (50 ml) and added to a 500 ml flask containing solid imidazole (17.1 g). To this a solution of tert-butyldimethylsilyl chloride (34 g) in dimethylformamide (120 ml) was added and reaction flask was cooled in an ice-bath. The reaction was quenched by addition of water-saturated ethyl acetate. The mixture was stirred at ambient temperature. To this water was added and the biphasic mixture was stirred for 1 hour. The mixture was then washed with water. The organic phases were mixed and washed with water to remove traces of dimethylformamide. The organic phase was evaporated under reduced pressure to yield (S)-benzyl-3-(tert-butyl dimethylsilyloxy)glutaramate.

Provenance & Evidence