1,1'-Carbonyldiimidazole → (R)-3-[3,5-Dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one

Participants

Reaction Steps

Treat a solution of (R)-3′,5′-dichloro-4′-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid (0.337 g, 0.545 mmol) in CH2Cl2 (20 mL) with 1,1′-carbonyldiimidazole (0.177 g, 1.09 mmol) and stir for 45 minutes at room temperature. Treat the reaction with 4-trifluoromethylpiperidine hydrochloride (0.155 g, 0.818 mmol) and diisopropylethylamine (0.106 g, 0.818 mmol) and stir for 12 hours at room temperature. Load the mixture on a silica gel column, flash with 25% to 50% ethyl acetate in hexanes to afford 0.34 g (84%) of the title compound. MS (m/z): 754 (M+).

Provenance & Evidence