(1S,3R)-1-(Boc-amino)-3-(Cbz-amino)cyclopentane → 1,1-Dimethylethyl N-[(1S,3R)-3-aminocyclopentyl]carbamate

Participants

Reaction Steps

A mixture of ((1S,3R)-3-benzyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester (635 mg, 1.90 mmol) and 10% Pd on carbon (202 mg, 0.19 mmol) in ethanol (15 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 16 hours. The reaction mixture was filtered through Celite® which was washed with ethanol and the filtrate concentrated under vacuum to afford 390 mg (quant.) of ((1S,3R)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester as a colorless oil. LCMS (Method H, ESI): RT=0.38 min, m+H=200.9; 1H NMR (400 MHz, DMSO) δ: 6.82 (d, 1H), 3.75-3.66 (m, 1H), 3.17 (m, 2H), 1.98 (m, 1H), 1.70 (m, 3H), 1.49 (m, 1H), 1.37 (s, 9H), 1.31 (m, 1H), 1.14 (m, 1H).

Provenance & Evidence