HCID 86707712, compound → HCID 86707713, compound

Participants

Reaction Steps

To a flask, charged with 10% palladium on carbon (90 mg, 0.845 mmol), under a steady nitrogen flow was added ethanol (5 ml), followed by addition of a solution of (1S,3R)-methyl 3-(benzyloxycarbonylamino)-1,2,2-trimethylcyclopentanecarboxylate (900 mg, 2.82 mmol) in ethanol (11.300 ml). The flask was evacuated and flushed with hydrogen and then filled with one atmosphere of hydrogen. The reaction was stirred at room temperature for 14 hrs. The flask was evacuated and backfilled with nitrogen. The suspension was filtered through a pad of Celite. The Celite cake was washed with ethanol (3×, 20 ml). The ethanol wash was concentrated under reduced pressure to yield the title compound (478 mg, 2.58 mmol, 92% yield) as a colorless oil. LC/MS found [M+H]+=186.3. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.68 (s, 3H), 3.10 (t, J=9.1 Hz, 1H), 2.57-2.47 (m, 1H), 2.11-2.02 (m, 1H), 1.46-1.35 (m, 2H), 1.19-1.17 (m, 3H), 1.07-1.03 (m, 3H), 0.72 (s, 3H).

Provenance & Evidence