tert-butyl 4-(2-fluoro-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-amino-2-fluorophenyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(2-fluoro-4-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (A27) (0.391 g, 1.20 mmol) in EtOAc (10 mL) was added 10% Pd/C (0.118 g) in EtOAc (1 mL) and the resulting suspension was stirred at 30° C. under a hydrogen atmosphere for 16 hours. The resulting mixture was filtered through Celite and the filtrate concentrated under reduced pressure to give the title compound A28 (0.339 g, 96%); 1H NMR (400 MHz, CDCl3) δ 6.94 (dd, J=8.3 Hz, 1H), 6.41 (dd, J=8.2, 2.4 Hz, 1H), 6.36 (dd, J=12.1, 2.3 Hz, 1H), 4.21 (brs, 2H), 3.65 (s, 2H), 2.84 (m, 3H), 1.75 (bd, J=13.3 Hz, 2H), 1.47 (s, 9H).

Provenance & Evidence