Sodium hydride → tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

DMSO (200 ml) was added to sodium hydride (60% NaH, 24.0 g), and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was cooled to room temperature and THF (200 ml) was added. The mixture was cooled to -5° C., and thereto was dropwise added a solution of trimethylsulfonium iodide (122.5 g) in DMSO (400 ml). After stirring for 1 minute, a solution of N-(tert-butoxycarbonyl)-L-prolinal (60.0 g) in THF (200 ml) was added quickly, followed by stirring at 0° C. for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give the crude product of the title compound (54.9 g), which was then used in the next reaction without purification.

Provenance & Evidence