反应详情

To a solution of 2,3,4,5-tetrahydro-1H-benzo[B]azepine (0.37 g), triethylamine (0.35 mL) and 4-dimethylaminopyridine (26 mg) in methylene chloride (8 mL) was added 4-fluoro-3-nitrobenzenesulfonyl chloride (0.5 g), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in tetrahydrofuran (7 mL). To the solution were added methanol (7 mL) and nickel(II) bromide (23 mg). To the mixture was added sodium borohydride (0.24 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes, and then stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1) to give the title compound (0.26 g).

1. extractionthe resulting mixture was extracted with ethyl acetate
2. washThe extract was washed with 1 mol/L hydrochloric acid, water and brine successively
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was removed under reduced pressure
5. dissolutionthe residue was dissolved in tetrahydrofuran (7 mL)
6. additionTo the solution were added methanol (7 mL) and nickel(II) bromide (23 mg)
7. additionTo the mixture was added sodium borohydride (0.24 g) under ice-
8. temperaturecooling
9. stirringthe mixture was stirred at the same temperature for 30 minutes
10. stirringstirred at room temperature for 30 minutes
11. additionTo the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution
12. extractionthe resulting mixture was extracted with ethyl acetate
13. washThe extract was washed with water and brine
14. dry with materialdried over anhydrous magnesium sulfate
15. customThe solvent was removed under reduced pressure
16. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=1/1)