Ethyl Acetate → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

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Reaction Steps

80% m-Chloroperbenzoic acid (3.9 g, 0.0226 mole) was added to a solution of 2,5-dihydro-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester (3.55 g, 0.021 mole) in dichloromethane (70 ml) and the mixture was stirred for 24h when more peracid (0.27 g,0.00156 mole) was added and the stirring continued for a further 4h. Ethyl acetate was added and the mixture was washed with 10% sodium carbonate solution. The aqueous phase was extracted with ethyl acetate (50 ml) and the combined organic solution washed with water, dried (MgSO4) and evaporated to leave an oil which was purified by column chromatography on flash silica eluting with 30% ethyl acetate in cyclohexane to give the title compound (1.52 g) as an oil, nmr(δ,CDCl3) includes 1.45(s,9H), 3.42(dd,2H), 3.67(s,2H), 3.78(dd,2H).

Provenance & Evidence