m-Chloroperbenzoic acid → (3R)-3-(Benzylsulfinyl)methyl-1-(tert-butoxycarbonyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (3R)-3-(benzylthio)methyl-1-(tert-butoxycarbonyl)pyrrolidine (0.2553 g, 0.830 mmol) in ethyl acetate (15 ml), under argon, cooled in a bath at ca. -40° C., was added portionwise 57-86% 3-chloroperoxybenzoic acid (0.2094 g). The mixture was then allowed to warm to 0° C. over 1.5 h, before pouring into 5% NaHCO3 solution (15 ml). The organic layer was separated and washed with more 5% NaHCO3 solution (15 ml), then saturated NaCl solution (10 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2) to give 0.2381 g (89%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 1.44 (9H, s), 1.61 (1H, m), 2.15 (1H, m), 2.52 (1H, m), 2.66 (2H, m), 3.00 (1H, m), 3.29 (1H, m), 3.43 (1H, m), 3.63 (1H, m), 3.96 (1H, d, J=12.9 Hz), 4.07 (1H, d, J=12.9 Hz), 7.28-7.30 (2H, m), 7.35-7.39 (3H, m). m/e (ES+) 324 (M+H)+.

Provenance & Evidence