反应详情

To a solution of 2.17 mmol of 1-benzyl-8-methoxy-4,5-dihydro-1H-benzo[c]azepin-3(2H)-one in tetrahydrofuran under nitrogen atmosphere was added 3.25 mmol of lithiumaluminumhydride as 1 M solution in tetrahydrofuran. The solution was heated to reflux and stirred for 1.5 h. The mixture was cooled to room temperature and water (1 ml) was carefully added. The mixture was concentrated and the residue was dissolved in ethyl acetate. The organic phase was extracted with acidified water (acidified with 1 M HCl, 4×). To the combined aqueous phase was added NaOH (50%) until basic and ethyl acetate. The suspension was filtered over celite. The residue was washed with water and ethyl acetate. Phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. Evaporation of the solvent gave 439 mg of crude material that was purified by flash chromatography to yield 399 mg of 1-benzyl-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine (69%).

1. temperatureThe solution was heated
2. temperatureto reflux
3. concentrationThe mixture was concentrated
4. dissolutionthe residue was dissolved in ethyl acetate
5. extractionThe organic phase was extracted with acidified water (acidified with 1 M HCl, 4×)
6. additionTo the combined aqueous phase was added NaOH (50%) until basic and ethyl acetate
7. filtrationThe suspension was filtered over celite
8. washThe residue was washed with water and ethyl acetate
9. customPhases were separated
10. extractionthe aqueous layer was extracted with ethyl acetate
11. dry with materialThe combined organic layers were dried over MgSO4
12. filtrationfiltered
13. customEvaporation of the solvent
14. customgave 439 mg of crude material that
15. customwas purified by flash chromatography