Carbamic acid, [(1S,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI)

99027-90-4

167465-99-8

Tert-butyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (8.0 g, 40.56 mmol, 1.00 eq.) was mixed with palladium/carbon catalyst (0.5 g) in methanol (100 mL). The reaction was stirred at 60 °C for 48 hours under hydrogen atmosphere. Upon completion of the reaction, the mixture was cooled to room temperature and the catalyst was removed by filtration. The catalyst was washed with methanol (3 x 10 mL). The filtrate and washings were combined and concentrated in vacuum to give tert-butyl N-[(1S,3R)-3-hydroxycyclopentyl]carbamate (6.5 g, 80% yield) as a white solid. The product was characterized by 1H NMR (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).