Hydrochloric Acid → (S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one

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Reaction Steps

Imidazole (93.73 g, 1.26 mol) and tert-butyldimethylsilyl chloride (145.3 g, 0.96 mol) were added to a solution of (S)-4-hydroxy-2-pyrrolidone (92.8 g, 0.92 mol) in dimethylformamide (560 mL). The mixture was then stirred at room temperature for 16 hours, after which time it was poured over ice and an aqueous solution of hydrochloric acid (0.2 M, 300 mL) was added. The mixture was stirred at room temperature for 10 minutes, and then extracted with ethyl acetate (4×500 mL). The combined organic extracts were washed with brine (1000 mL), dried over sodium sulphate, filtered, and evaporated under reduced pressure to give (S)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one as a solid (200 g, 100%).

Provenance & Evidence