Ammonium formate → 3-(RS)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine

Participants

Reaction Steps

A mixture of 232 mg (0.6 mmol) of 1-phenylmethyl-3-(SR)-((4-phenyl) piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine (from Example 9, Step B), 894 mg (14.1 mmol) of ammonium formate and 116 mg of 20% Pd(OH)2 on carbon in 10 mL of MeOH was heated at reflux for 1 h. The reaction mixture was cooled and filtered througha pad of Celite. The reaction flask and filtered solids were rinsed with 50 mL of EtOAc and the filtrate was concentrated in vacuo. The residue was partitioned between 50 mL of EtOAc and 30 mL of sat'd NaHCO3 and the layers were separated. The organic layer was dried over MgSO4. The aqueous layer was extracted with 50 mL of EtOAc; the extract was dried and the organic layers were combined and concentrated in vacuo to afford 190 mg (95%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ1.63-1.80 (m, 4H), 1.93-2.05 (m, 2H), 2.39-2.53 (m, 5H), 2.83 (d, J=10.7, 1H), 2.93-3.02 (m, 2H), 3.08 (t, J=9.6, 1H), 3-47-3.53 (m, 1H ), 5.19 (br s, 1H ), 7.19-7.38 (1OH). Mass Spectrum (NH3 -CI): 321 (M+1).

Provenance & Evidence