Ethyl Acetate → 2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cycloheptyl-ethanol

Participants

Reaction Steps

To a solution of 1.4 g (3.13 mmol) [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cycloheptyl-acetic acid ethyl ester in 20 ml dry tetrahydrofuran was added 0.125 g (3.29 mmol) lithium aluminum hydride at 0° C. The reaction mixture was stirred for 2 hours at room temperature and then poured on 100 ml 10% aqueous sodium-potassium-tartrate solution and 100 ml ethyl acetate. The aqueous layers were extracted again with 100 ml ethyl acetate. The organic layers were washed with 100 ml brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (2:1). Colorless solid (74%). MS (TurboSpray): 405.3 [M+H].

Provenance & Evidence