Sodium borohydride → (S)-N-(1-Ethyl-3-methyl-1H-pyrazol-4-yl)-2-hydroxy-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-2-oxo-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide (145 mg, 0.34 mmol) was dissolved in MeOH (4 mL), cooled to 0° C. and treated with NaBH4 (38 mg, 1 mmol) and stirred for 12 h at ambient temperature. The reaction mixture was quenched with aqueous K2CO3 (2 M, 1 mL), concentrated, then redissolved in EtOAc (15 mL) and washed with aqueous K2CO3 (2 M, 3×15 mL). The combined aqueous layers were extracted with EtOAc (3×15 mL) and the combined organic layers dried over sodium sulfate. Concentration afforded the racemic compound (170 mg, >100%) as a light yellow oil. Separation by chromatography on a chiral column provided the title compound as a colourless oil (38 mg, 26%) MS m/e: 433.2 [M+H]+ which crystallized upon standing.

Provenance & Evidence