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

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Reaction Steps

To a 0° C. solution of phenylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylate (10.30 g, 50.68 mmol) in DCM (250 mL) was added m-CPBA (wet; ca. 75%; 17.49 g). The solution was stirred and warmed to room temperature overnight. The solution was diluted with DCM and washed with 2×10% aq. NaHCO3-1 N aq. NaOH (1:1). The organic phase was dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and purified by silica gel chromatography (40% EtOAc in hexanes) to give phenylmethyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (7.90 g, 71% yield) as a light yellow oil.

Provenance & Evidence