Acetic Acid → 2-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetic acid

Participants

Reaction Steps

Cyclohex-1-ene-1-carbaldehyde (25.9 μl, 0.227 mmol), acetic acid (30 μl) and sodium triacetoxyborohydride (68.8 mg, 0.325 mmol) were added to a solution of 2-[(3R*,4S*)-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-4-methyl-3-[(piperidin-4-yl)carbamoyl]pyrrolidin-3-yl]acetic acid obtained by the method of Example 5d (15 mg, 0.0325 mmol) in tetrahydrofuran (dehydrated) (2 mL), followed by stirring overnight. Water and methanol were added to the reaction liquid, which was concentrated under reduced pressure, and the residue was purified by ODS column chromatography (elution solvent: water/methanol) to give the title compound (12.8 mg, yield: 70.8%).

Provenance & Evidence