反应详情

2-[3-(2-Naphthyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]ethanol (0.95 g, 3.40 mmol), 0.42 g (3.70 mmol) MsCl, 0.71 mL (515 mg, 5.10 mmol) Et3N and 20 mL CH2Cl2 are stirred at 23 C in for 12 h. The reaction mixture is poured into 200 mL of H2O and extracted with 3×50 mL CH2Cl2. The combined organics are washed with H2O (3×100 mL,) brine (1×100 mL), dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography on SiO2 gel, eluting with EtOAc/MeOH (20/1 to 10/1), gives 0.50 g (1.68 mmol, a 50% yield) of the title compound as a tan solid. mp: 122-123° C.; MS (ES) m/z 298 (MH)+.

1. extractionextracted with 3×50 mL CH2Cl2
2. washThe combined organics are washed with H2O (3×100 mL,) brine (1×100 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customthe volatiles are evaporated
6. washFlash chromatography on SiO2 gel, eluting with EtOAc/MeOH (20/1 to 10/1)
7. customgives 0.50 g (1.68 mmol