反应详情

温度

-78 °C

To a stirred solution of tert-butyl 2-[(tert-butoxycarbonyl)amino]-2-(3,5-difluorophenyl)propanoate (27.0 g, 76 mmol) in THF (350 mL) at −78° C. was added LiAlH4 (76 mL of a 1 M solution in THF, 76 mmol), dropwise. The reaction mixture was stirred at −78° C. for 3 h, then quenched with EtOAc (76 mL), then H2O (228 mL), then 1 N aqueous NaOH (76 mL), then EtOAc (228 mL). The reaction mixture was warmed to ambient temperature, stirred for 1 h, filtered, and extracted with EtOAc (2×450 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with hexane:EtOAc—100:0 to 70:30, to give the title compound. MS: m/z=186 (M−CO2C4H7).

1. customquenched with EtOAc (76 mL)
2. temperatureThe reaction mixture was warmed to ambient temperature
3. stirringstirred for 1 h
4. filtrationfiltered
5. extractionextracted with EtOAc (2×450 mL)
6. dry with materialThe organic extracts were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by silica gel chromatography
10. washeluting with hexane