Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 2-(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(4-chloro-phenyl)-4-hydroxymethyl-piperidin-1-yl]-ethanone

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Reaction Steps

In a 25 mL flask was taken 500 mg of [4-(4-chloro-phenyl)-piperidin-4-yl]-methanol (2.44 mmol, 1.0 equiv), 591 mg of (4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (2.44 mmol, 1.00 equiv), 1.29 g BOP (2.92 mmol, 1.2 equiv), 1.36 mL TEA (9.75 mmol, 4.00 equiv) and 15 mL NMP. A stir bar was placed in the flask and the mixture stirred overnight at room temperature under N2. The crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent) to yield 2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(4-chloro-phenyl)-4-hydroxymethyl-piperidin-1-yl]-ethanone. MS (ES) M+H expected=450.0, found=450.3

Provenance & Evidence