HCID 53410921, compound → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Participants

Reaction Steps

A solution of [trans-(+/-)]-3-hydroxy-4-[(phenylmethyl)amino]-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester (1.1 g, 3.76 mmol) in ethanol (150 ml) was hydrogenated over 10% palladium-on-carbon (0.05 g) for 3.5h. The catalyst was removed by filtration, washed with ethanol (50 ml) and the combined ethanolic solution was evaporated to leave an oil which was taken up in ethyl acetate (75 ml). The solution was filtered and the filtrate evaporated to leave a solid which was crystallised from ethyl acetate/cyclohexane to give the title compound (0.643 g), nmr(δ,CDCl3) 1.45(s, 9H), 1.6-2.2(bm, 3H), 3.1(m,1H), 3.3(m,2H), 3.68(m,2H), 3.98(m,1H).

Provenance & Evidence