反应详情

温度

-78 °C

To a cooled (−78° C.) solution of KHMDS (3.49 mL, 1.745 mol, 0.5 M in toluene) in 5 mL of THF was added a cooled (−78° C.) solution of (R)-3-(6-(4-fluoro-3-methylbenzyloxy)hexanoyl)-4-benzyloxazolidin-2-one (0.481 g, 1.163 mmol) in 4 mL of THF. The reaction was stirred at −78° C. under N2 for 1 h. Then a cooled (−78° C.) solution of trisyl azide (0.448 g, 1.454 mmol) in 4 mL of THF was added. After 1-2 min, a solution of HOAc (0.321 g, 5.350 mmol) in 4 mL of THF was added. After warmed slowly to room temperature and stirred for overnight, the reaction mixture was diluted with brine (50 mL) and extracted with dichloromethane (40 mL×3). The combined organic extracts 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 (0.252 g, 48% yield). FT-IR (neat): 2104, 1778, 1704 cm−1.

1. additionwas added
2. additionwas added
3. waitAfter 1-2 min
4. temperatureAfter warmed slowly to room temperature
5. stirringstirred for overnight
6. extractionextracted with dichloromethane (40 mL×3)
7. dry with materialThe combined organic extracts dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe product was isolated by Flash column chromatography (silica gel column)
11. washeluting with 0-100% dichloromethane/hexanes