m-Chloroperbenzoic acid → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

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Reaction Steps

2,5-Dihydro-pyrrole-1-carboxylic acid tert-butyl ester (46 g, 65% purity) was dissolved in CH2Cl2 (500 mL). The solution was cooled to 0° C. mCPBA (122 g, 2 eq, 77% purity) was slowly added to the solution at 0° C. The reaction mixture was stirred at 0° C. to RT for overnight. The mixture was concentrated to 200 ml, and filtered. The organic phase was washed with 1 N NaOH solution (4×100 mL), dried over Na2SO4. The resulting oil was purified by column chromatography (hexane:ethyl acetate 3:1) to give 28 g of desired product as a colorless oil (87% yield). 1H-NMR (300 MHz, CDCl3): δ 1.41 (s, 9H), 3.26 (dd, 2H), 3.25-3.80 (m, 4H)

Provenance & Evidence