m-Chloroperbenzoic acid → Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

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Reaction Steps

To solution of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (10.0 g, 49.2 mmol) in dichloromethane (197 mL) at 0° C. was added m-CPBA (16.98 g, 98 mmol) in several portions and the resulting mixture was allowed to warm to rt and stir overnight. The resulting white heterogeneous mixture obtained was diluted with dichloromethane (150 mL) and aq. sat. sodium bicarbonate (150 mL). The mixture was stirred and the resulting layers were separated and the organic portion was washed successively with aq. sat. sodium bicarbonate (150 mL), water, brine, before drying over anhyd. sodium sulfate, filtering and concentrating in vacuo to a colorless oil (˜14 g). This crude material was subjected to purification by preparative chromatography using Hex/EtOAc mixtures as the eluant and an 80 g silica gel cartridge. Fractions containing the major product were combined and concentrated to afford the title compound (9.60 g, 43.8 mmol, 89%) as a colorless oil. LCMS: 220.2 (M+H)+; 1H NMR (400 MHz, METHANOL-d4): δ 7.41-7.31 (m, 4H), 5.14 (d, J=1.1 Hz, 2H), 3.84-3.74 (m, 4H), 3.42 (t, J=13.8 Hz, 2H).

Provenance & Evidence