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

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.

1. stirringthe reaction mixture was stirred at 80° C. for 2 hours
2. filtrationThe reaction mixture was filtered over CELITE
3. temperaturewhile still warm
4. concentrationThe filtrate was concentrated in vacuo
5. additiondiluted with water
6. extractionextracted with ethyl acetate
7. washwashed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

ORD record

ord-dcee7ccdedb44ae0aaf10b07247be04a

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353066B2