反应详情

To a solution prepared by dissolving 8.26 g (36.0 mM) of 2-(1-tert-butoxycarbonylpiperidin-4-yl)ethanol and 10.0 ml (72.0 mM) of triethylamine in 50 ml of ether was added 3.34 ml (43.2 mM) of methanesulfonyl chloride dropwise at 0° C. After completion of dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured in 100 ml of iced water and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate (MgSO4) and the solvent was distilled off under reduced pressure to recover the mesylate as solid. To a solution prepared by dissolving this mesylate and 10.37 g (36.0 mM) of 1,2-dihydro-1,4,7b-triazacyclopent[cd]inden-2-one.2NaCl in 25 ml of DMF was added 6.46 ml (43.2 mM) of DBU and the mixture was heated at 80° C. for 2 hours. After completion of the reaction, the reaction mixture was poured in iced water and the mixture was extracted with 200 ml of ethyl acetate. The organic layer was washed with 200 ml of purified water 3 times and further with 200 ml of saturated aqueous NaCl solution and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to provide 9.10 g (yield 68.2%) of the title compound as light-yellow solid.

1. customTo a solution prepared
2. additionAfter completion of dropwise addition
3. customAfter completion of the reaction
4. extractionthe mixture was extracted with 100 ml of ethyl acetate
5. washThe organic layer was washed with 100 ml of saturated aqueous NaCl solution
6. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
7. distillationthe solvent was distilled off under reduced pressure
8. customto recover the mesylate as solid
9. customTo a solution prepared
10. temperaturethe mixture was heated at 80° C. for 2 hours
11. customAfter completion of the reaction
12. extractionthe mixture was extracted with 200 ml of ethyl acetate
13. washThe organic layer was washed with 200 ml of purified water 3 times and further with 200 ml of saturated aqueous NaCl solution
14. dry with materialdried over MgSO4
15. distillationThe solvent was then distilled off under reduced pressure
16. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)