Water → 3,5-Difluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3,5-difluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester in anhydrous THF (5 mL) at 0° C. was added 2M LiBH4 solution in THF (0.5 mL). The solution was allowed to warm to 25° C. and stir for 18 h. LC-MS of a reaction aliquot revealed unreacted starting material present. The reaction solution was immersed in an ice bath and 2M lithium borohydride (0.5 mL) was added and the solution allowed to warm to 25° C. and was stirred for 18 h. This procedure was repeated once more and, after 72 h, water was added to quench the reaction. The solvent was removed to give a tan solid which was transferred to a separatory funnel with EtOAc (100 mL) and washed with 1M citric acid solution (100 mL×2). The aqueous washings were combined and extracted with EtOAc (100 mL). The organic extracts were combined, washed with brine (100 mL), dried (MgSO4), filtered and evaporated to give a peach colored solid (300 mg). This residue was adsorbed onto silica gel and purified by column chromatography, eluting with a solution of 50% EtOAc in hexanes to afford the alcohol (119 mg, 51%) as a white solid. Mass Spectrum (−ESI): 358.8 [M−H]−

Provenance & Evidence