m-Chloroperbenzoic acid → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

Participants

Reaction Steps

To a stirring solution of 3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (6.27 g, 34.2 mmol) in dichloromethane (35 mL) cooled down to 0° C. was added dropwise a solution of m-chloroperoxybenzoic acid (8.65 g, 1.1 eq) in dichloromethane (50 mL). The mixture stirred at room temperature for 4 hours. The mixture was partitioned between dichloromethane and 5% potassium carbonate solution. The combined organic layers were washed with brine, separated and dried (MgSO4). The crude product was purified by column chromatography to yield a (±)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (4.43 g) as a pale yellow liquid.

Provenance & Evidence