HCID 57526945, compound → HCID 57526936, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-(5-{[(benzyloxy)carbonyl]amino}-2,4-difluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (1.60 g, 3.60 mmol) and 5% Pd/C (320 mg, 0.100 mmol) in ethyl acetate (25.0 mL) and methanol (25.0 mL) was hydrogenated at room temperature for 72 hours using hydrogen bomb (200 psi). The reaction mixture was filtered through Celite and washed with EtOAc/MeOH (1:1, 3×50 mL). The filtrate was concentrated in vacuo to afford tert-butyl 4-(5-amino-2,4-difluorophenyl)-1-piperidinecarboxylate (1.39 g, 100%). 1H NMR (400 MHz, CDCl3) δ 6.73 (t, 1H, J=10.6 Hz), 6.60-6.54 (dd, 1H, J=7.6, 6.57 Hz), 4.20 (br, 2H), 3.55 (s, 2H), 2.96-2.72 (m, 3H), 1.79-1.71 (m, 2H), 1.58-1.52 (m, 2H), 1.47 (s, 9H); ESMS m/e: 257.3 (M−56).

Provenance & Evidence