反应详情

Palladium-on-charcoal (5%, 120 mg) was added to a solution of 2-[4-dimethylamino-4-(3-fluorophenyl)-cyclohexylidene]-N-[2-(1H-indol-3-yl)-ethyl]-acetamide (base of Example 25; 660 mg; 1.55 mmol) in abs. methanol (100 ml). The reaction mixture was hydrogenated at 40° C. under a pressure of 3 bar for 20 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue by chromatography on silica gel (45 g) with EA/methanol (5:1) and methanol, the less polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)ethyl]acetamide was isolated in a yield of 13% (86 mg) and the more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)ethyl]acetamide was isolated in a yield of 59% (391 mg). Both amides were colourless oils and diastereomerically 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 (45 g) with EA/methanol (5:1) and methanol