Ammonium Chloride → (1R)-1-(3',5'-diaminobiphenyl-4-yl)-2,2-difluoroethanol

Participants

Reaction Steps

Ammonium chloride (102 mg, 1.91 mmol) was added to a stirred (room temperature) mixture of (1R)-1-(3′,5′-dinitrobiphenyl-4-yl)-2,2-difluoroethanol (517 mg, 1.60 mmol) and iron (1070 mg, 19.1 mmol) in ethanol (5.32 mL) and water (2.66 mL), and then the reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was filtered over CELITE while still warm. The filtrate was concentrated in vacuo, diluted with water, extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) afforded (1R)-1-(3′,5′-diaminobiphenyl-4-yl)-2,2-difluoroethanol. MS ESI calc'd. for C14H15F2N2O [M+H]+ 265, found 265.

Provenance & Evidence