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

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Reaction Steps

22.1 A solution of 19.6 g N-Boc-pyrroline in 200 ml CH2Cl2 was cooled to −10° C. and was treated in two portions with 30 g meta-chloroperbenzoic acid. The mixture was stirred for 17 h, slowly warming up to room temperature. Then, the white precipitate was filtered off and washed with dichloromethane. The filtrate was washed with 5% aq. NaHSO3, sat. aq. NaHCO3 and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 65:35) to give 11.8 g 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester as a light yellow oil. MS 186.1 ([M+H]+)

Provenance & Evidence