反应详情

温度

0 °C

A solution of 2.5 eq of diisopropylamine in 50 mL of dry THF was cooled to −78° C. While stirring, 2.4 eq of n-BuLi (2.5 M in hexanes) was added dropwise. The reaction mixture was warmed to 0° C. After stirring for 30 min, the solution was cooled to −78° C. and 1.0 eq of 97 dissolved in 20 mL of dry THF was added. After stirring at −78° C. for 30 min, 1.5 eq of trisyl azide was added. The mixture was stirred, as it warmed to rt. After 17 hrs, 4.5 eq of 17 M glacial acetic acid was added and stirred at rt for 5 hrs. The reaction mixture was rotary evaporated and 30 mL of saturated NaHCO3 was added. The mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were dried over MgSO4 and vacuum filtered. The filtrate was rotary evaporated and flash chromatographed on silica using EtOAc as eluent. After concentration and drying under vacuum of the fractions containing product, a brownish colored solid was obtained as 98.

1. stirringAfter stirring for 30 min
2. temperaturethe solution was cooled to −78° C.
3. additionwas added
4. stirringAfter stirring at −78° C. for 30 min
5. stirringThe mixture was stirred, as it
6. temperaturewarmed to rt
7. stirringstirred at rt for 5 hrs
8. customThe reaction mixture was rotary evaporated
9. addition30 mL of saturated NaHCO3 was added
10. extractionThe mixture was extracted with EtOAc (3×50 mL)
11. dry with materialThe combined organic extracts were dried over MgSO4 and vacuum
12. filtrationfiltered
13. customThe filtrate was rotary evaporated
14. customflash chromatographed on silica
15. concentrationAfter concentration
16. customdrying under vacuum of the fractions
17. additioncontaining product
18. customa brownish colored solid was obtained as 98