Ethyl (1R,2R,3S,6S)-6-[(benzylamino)methyl]-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylate → Ethyl (1R,2R,3S,6S)-6-(aminomethyl)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylate

Participants

Reaction Steps

To a solution of the crude oil from Step D (0.15 g, 0.24 mmol) in 40 mL ethanol was added 0.1 g (20% by weight) of 10% Pd(OH)2—C. The mixture was hydrogenated at 50 PSi for 16 hr at room temperature. The catalyst was filtered through a filter aid pad. The solvent of the filtrate was removed under vacuum to give the title compound (0.09 g) which was used without further purification. 1H-NMR (CDCl3) δ: 7.71 (1H, s), 7.20 (2H, s), 7.00 (2H, m), 6.85 (2H, m), 4.45 (1H, q, J=6.4 Hz), 3.83 (2H, m), 3.35 (1H, m), 3.00-2.86 (2H, m), 2.75 (1H, m), 2.52 (1H, t, J=11.0 Hz), 2.40 (1H, m), 2.25 (1H, m), 1.58 (1H, m), 1.40 (1H, m), 1.33 (3H, d, J=6.4 Hz), 0.88 (3H, t, J=7.1 Hz). MS: (MH)+ 536.5.

Provenance & Evidence