Toluene → HCID 121317066, compound

Temperature

-78 °C

To a solution of ethyl (S)-3-(((R)-tert-butylsulfinyl)amino)-2,2,4,4-tetrafluoro-3-(2-fluorophenyl)-butanoate (3.20 g, 7.97 mmol) in dry THF (35 mL) was added dropwise a solution of DIBAL-H (diisobutylaluminium hydride) in toluene (1.0 M, 16 mL, 16 mmol) at −78° C. under N2. The mixture was stirred at −78° C. for 2 hours. The reaction was quenched carefully with methanol (3 mL) at −78° C. Then water (20 mL) and ethyl acetate (200 mL) were added and the mixture was warmed to 25° C. The mixture was aged for 30 minutes. The resulting mixture was filtered through a Celite pad. The organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated to give crude product (R)-2-methyl-N—((S)-1,1,3,3-tetrafluoro-2-(2-fluorophenyl)-4-oxobutan-2-yl)propane-2-sulfinamide, which was used immediately in the next step without further purification.

1. customThe reaction was quenched carefully with methanol (3 mL) at −78° C
2. additionThen water (20 mL) and ethyl acetate (200 mL) were added
3. temperaturethe mixture was warmed to 25° C
4. waitThe mixture was aged for 30 minutes
5. filtrationThe resulting mixture was filtered through a Celite pad
6. washThe organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. concentrationThe organic layer was concentrated

ORD record

ord-b735f6d720c347d38d2eda7e001160ec

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346797B1