反应详情

温度

-10 °C

To a cooled (−10° C.) solution of 8-(4-fluoro-3-methylphenyl)octanoic acid (0.452 g, 1.791 mmol) in 15 mL of THF, were added stepwise triethylamine (0.67 mL, 4.836 mmol) and pivaloyl chloride (0.24 mL, 1.971 mmol). The reaction mixture was stirred at −10° C. for 1 h and then LiCl (0.084 g, 1.971 mmol) and (R)-4-benzyloxazolidin-2-one (0.349 g, 1.971 mmol) were added stepwise. After warming slowly to room temperature and stirring overnight, the reaction mixture was diluted with ethyl acetate (80 mL) and washed with saturated NaHCO3 solution and brine. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-100% dichloromethane/hexanes to give the title compound as colorless oil (0.666 g, 90% yield). GC-MS: tR=9.6 min; m/z 411 (M+).

1. temperatureAfter warming slowly to room temperature
2. stirringstirring overnight
3. washwashed with saturated NaHCO3 solution and brine
4. dry with materialThe organic layer was dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe product was isolated by Flash column chromatography (silica gel column)
8. washeluting with 0-100% dichloromethane/hexanes