Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate → tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Participants

Reaction Steps

Pd/C (10%; 510 mg) was added to a solution of tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate (A111) (2.21 g, 6.86 mmol) in methanol (30 mL) and the resulting mixture was stirred under a hydrogen atmosphere overnight. The mixture was filtered through Celite and the filtrate concentrated under reduced pressure to afford the title compound A112 (1.13 g, 56%); 1H NMR (300 MHz, CDCl3); δ 6.68 (d, J=8.8 Hz, 2H), 6.52 (d, J=8.7 Hz, 2H), 4.17 (m, 1H), 3.63 (m, 4H), 3.20 (m, 2H), 1.78 (m, 2H), 1.61 (m, 2H), 1.40 (s, 9H). LCMS-B: rt 5.05 min; m/z 293.2 [M+H]+.

Provenance & Evidence