(1S,2S)-2-[(E)-3-(4-Acetylamino-4-phenyl-piperidin-1-yl)-propenyl]-1-(3,4-dichloro-phenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide → (1S,2R)-2-[3-(4-Acetylamino-4-phenyl-piperidin-1-yl)-propyl]-1-(3,4-dichlorophenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide

Participants

Reaction Steps

(1S,2S)-2-[(E)-3-(4-Acetylamino-4-phenyl-piperidin-1-yl)-propenyl]-1-(3,4-dichloro-phenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide (65 mg, 0.11 mmol) is dissolved in dichloromethane (10 ml). N2 is bubbled through the solution for 15 minutes before adding Crabtree's catalyst (17.7 mg, 0.022 mmol, [(1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate]). The reaction mixture is hydrogenated at a Parr apparatus (ambient temperature, 3 atm. H2) for 3 hours. The solvent is removed by evaporation and the residue is subjected to silica gel chromatography eluting with ethyl acetate:ethanol:triethylamine (95:0:5)-(85:10:5). Evaporation from heptane furnishes the title compound as a white solid. Yield 25 mg (38%).

Provenance & Evidence