Tert-butyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate → 1,1-Dimethylethyl N-((1S,3R)-3-hydroxycyclopentyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (8.0 g, 40.56 mmol, 1.00 equiv) and palladium on carbon (0.5 g) catalyst in methanol (100 mL) was stirred under an atmosphere of hydrogen atmosphere at 60° C. for 48 h. The reaction mixture was cooled to room temperature and the catalyst was removed by filtration. The catalyst was washed with 3×10 mL of MeOH. The combined filtrate and washings was concentrated under vacuum to give 6.5 g (80%) of tert-butyl N-[(1S,3R)-3-hydroxycyclopentyl]carbamate as a white solid. 1HNMR (400 MHz, D2O, ppm) δ 4.72 (1H, s), 4.55 (1H, s), 1.92-1.87 (3H, m), 1.76-1.60 (3H, m), 1.50 (9H, s).

Provenance & Evidence