HCID 10345144, compound → 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone

Participants

Reaction Steps

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.

Provenance & Evidence