反应详情

温度

-78 °C

Treat a −78° C. solution of 3-[4-(tert-butyl-diphenyl-silanyloxy)-piperidin-1-yl]-pyrrolidin-2-one (0.25 g, 0.59 mmol) in THF (6 mL) with a 1.6 M n-butyl lithium in hexanes (0.37 mL, 0.59 mmol) and stir at −78° C. for 10 minutes under N2. Treat the reaction with 5-benzyloxy-2-bromomethyl-1,3-dichloro-benzene (0.204 g, 0.59 mmol), warm to room temperature, and stir for 16 hours under N2. Re-cool the reaction to −78° C., treat with 1.6 M n-butyl lithium in hexanes (0.37 mL, 0.59 mmol), warm to room temperature, and stir for 2 hours. Quench the reaction with water and extract with ethyl acetate. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 50 to 100% ethyl acetate in hexanes gradient to afford 0.263 g (65%) of the titled product. Rf=0.18 (3/1 ethyl acetate/hexanes). ES MS (m/z): 687 (M+).

1. additionTreat
2. temperaturewarm to room temperature
3. stirringstir for 16 hours under N2
4. customRe-cool the reaction to −78° C.
5. temperaturewarm to room temperature
6. stirringstir for 2 hours
7. customQuench
8. customthe reaction with water
9. extractionextract with ethyl acetate
10. dry with materialDry the organic layer (Na2SO4)
11. customremove the solvent in vacuo
12. customto afford crude product
13. custompurify with a 50 to 100% ethyl acetate in hexanes gradient