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

Participants

Reaction Steps

Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (24.00 g, 118 mmol) was dissolved in DCM (200 mL). Nitrogen was bubbled through it for ten minutes. Cooled to ˜0 degrees Celsius and added 3-chlorobenzoperoxoic acid (33.1 g, 148 mmol) in small portions with stirring. Let the suspension to stir overnight without removing the cold bath. The suspension was removed by filtration and the organic layer was washed with sat'd NaHCO3. The DCM soln. was dried (Na2SO4) and concentrated to give benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (22.5 g, 103 mmol, 87% yield). LCMS:M+23=242. Rt=1.57 min.

Provenance & Evidence