Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 1-[2-(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid methyl ester

Participants

Reaction Steps

In a 25 mL flask was added 4-(4-chloro-phenyl)-piperidine-4-carboxylic acid methyl ester hydrochloride (1.87 mmol, 1.0 equiv), 453 mg of (4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (1.87 mmol, 1.00 equiv), 990 mg BOP (2.24 mmol, 1.2 equiv), 1.04 mL TEA (7.46 mmol, 4.00 equiv) and 10 mL NMP. A stir bar was placed in the flask and the reaction mixture was stirred overnight at room temperature under N2 atmosphere. The crude product was purified by normal phase HPLC (EtOAc-hexane as the eluent) to yield 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid methyl ester: MS (ES) M+H expected=478.1, found=478.3.

Provenance & Evidence