tert-Butyl 4-(5-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(5-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of 354 (270 mg, 0.53 mmol) in methanol (25 mL) was added 10% palladium on charcoal (150 mg). The resulting mixture was purged with H2 gas and stirred under a hydrogen atmosphere for 3 days, filtered through a celite pad, evaporated and purified by flash chromatography, eluent 1:1 hexanes-ethyl acetate, to afford the title compound 355 as a white solid (24 mg, 10% yield). 1H NMR: (CD3OD) δ 7.73 (d, J=3.3 Hz, 1H), 7.45 (d, J=2.1 Hz, 1H), 7.34 (dd, J=8.2, 2.2 Hz, 1H), 7.23-7.19 (m, 2H), 7.01 (dd, J=4.7, 3.7 Hz, 1H), 6.96 (d, J=3.9 Hz, 1H), 6.88 (d, J=8.1 Hz, 1H), 4.17 (d, J=13.1 Hz, 2H), 3.00-2.90 (m, 2H), 2.04 (d, J=12.1 Hz, 2H), 1.60-1.54 (m, 2H).

Provenance & Evidence