1,3-Dimethyl-2-imidazolidinone → tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

DMI (350 ml) was added to a THF solution (1M, 350 ml) of sodium bis(trimethylsilyl)amide. After cooling the mixture to -13° C., a solution of N-(tert-butoxycarbonyl)-L-prolinal (57.71 g) and trimethylsulfonium iodide (73.9 g) in DMSO (350 ml) was dropwise added, and the mixture was stirred for 1 hour. The reaction mixture was poured into ice water and extracted with toluene. The extract was washed with 10% citric acid, a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to give a mixture (52.74 g) of two diastereomers of the title compound.

Provenance & Evidence