反应详情

Palladium on carbon (5%, 60 mg) was added to a solution of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexylidene]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone (605 mg, 1.36 mmole) in abs. methanol (100 ml). The reaction mixture was hydrogenated for 23 hours at RT under a pressure of 3 bar. The catalyst was separated using Celite and the filtrate was concentrated by evaporation. After chromatographic separation of the residue (579 mg) on silica gel (50 g) with EE/methanol (2:1) the non-polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone was isolated in a yield of 31% (190 mg), and the polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone was isolated in a yield of 64% (386 mg). Both compounds were colourless oils.

1. customThe catalyst was separated
2. concentrationthe filtrate was concentrated by evaporation
3. customAfter chromatographic separation of the residue (579 mg) on silica gel (50 g) with EE/methanol (2:1) the non-polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone
4. customwas isolated in a yield of 31% (190 mg)