反应详情

Palladium-on-charcoal (5%, 40 mg) was added to a solution of 2-[4-dimethylamino-4-(3-fluorophenyl)-cyclohexylidene]-N-[2-(1H-indol-3-yl)-1-methylethyl]-acetamide (417 mg, 0.96 mmol) in abs. methanol (40 ml). The reaction mixture was hydrogenated at RT under a pressure of 3 bar for 15 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue by chromatography on silica gel G [50 g; EA/MeOH (10:1)-(5:1)], the less polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide was isolated in a yield of 4% (15 mg) and the more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide was isolated in a yield of 41% (170.2 mg). Both products were colourless oils and diastereoisomerically pure.

1. customThe catalyst was separated off over Celite
2. concentrationthe filtrate was concentrated
3. customAfter separation of the residue by chromatography on silica gel G [50 g; EA/MeOH (10:1)-(5:1)]