Ethanol → 2-amino-5-(1,4-dioxaspiro[4.5]dec-8-yl)-N-methylbenzamide

Participants

Reaction Steps

10% Pd—C (50% H2O w/w) (264 mg, 0.124 mmol) was added to a solution of 2-amino-5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-methylbenzamide (Compound 139C, 357 mg, 1.24 mmol) in EtOH (30 mL, 500 mmol). The reaction mixture was subjected to three cycles of evacuation and N2 purging. After a fourth evacuation, the mixture was flushed with H2 and allowed to stirred under hydrogen overnight. The catalyst was removed by filtration through a pad of celite, and the filtrate was evaporated under reduced pressure to give the title compound as 333 mg of a pinkish solid. 1H NMR (400 MHz, DMSO-d6) δ 1.50-1.78 (m, 8H), 2.34-2.44 (m, 1H), 2.71 (d, J=4.55 Hz, 3H), 3.88 (t, J=2.40 Hz, 4H), 6.20 (s, 2H), 6.60 (d, J=8.34 Hz, 1H), 6.98 (dd, J=8.46, 1.89 Hz, 1H), 7.29 (d, J=2.02 Hz, 1H), 8.16 (d, J=4.55 Hz, 1H). MS (ES+): m/z=291.08 (100) [M+1]. HPLC: tR=2.60 min (ZQ3, polar—5 min).

Provenance & Evidence