Vertellus → HCID 86732222, compound

Participants

Reaction Steps

To a cooled (−15° C.) solution of (R)-N-((S)-2-(2,3-difluorophenyl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide (5.0 g, 12.84 mmol) in MeOH (20 mL) was added sodium borohydrate (0.729 g, 19.26 mmol). The resulting mixture was stirred at this temperature for 10 min. LCMS indicated reaction went to completion. The mixture was quenched with saturated NaHCO3, diluted with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the resulted residue was recrystallized in dichloromethane to afford (R)-N-((2S,4S)-2-(2,3-difluorophenyl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (2.49 g, 6.36 mmol, 49.5% yield) as white solid. The filtrate was the undesired diastereomers and no further purification was carried out. MS m/z=392.1 [M+H]+. Calculated for C15H19F6NO2S: 391.4

Provenance & Evidence