Ethyl Acetate → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-hydroxymethyl-N-methyl-5-trifluoromethyl-benzamide

Participants

Reaction Steps

To a solution of N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester (300 mg, 668 μmol, example 75) in THF (5 mL) was added LiAlH4 (26.6 mg, 702 μmol) at 0° C. The reaction mixture was stirred at this temperature for 1 hour. The reaction mixture was poured on 30 mL aqueous 10% potassium-sodium-tartrate solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (102 mg, 36%). MS (ESI): m/z=421.092 [M+H]+.

Provenance & Evidence