反应详情

温度

70 °C

The product from Step C (3.04 g, 18.3 mmol) was dissolved in ethanol (50 mL), ammonium acetate (1.55 g, 20.10 mmol) was added followed by nitroethane (2.75 g, 36.5 mmol). The reaction mixture was stirred at 70° C. for 3 h and then the solvent was removed. The residue was dissolved in ethyl acetate (100 mL) and washed with water (2×100 mL). The organic layer was dried (MgSO4) and concentrated to give a solid, which was dissolved in anhydrous tetrahydrofuran (100 mL) and cooled to 0° C. To this solution, a 1 M solution of lithium aluminum hydride in tetrahydrofuran (73 mL) was added and the reaction mixture allowed to warm to room temperature and stirred for 2 h followed by heating at reflux for an additional 2 h. Excess lithium aluminum hydride was consumed by adding ethyl acetate (50 mL) and then water (400 mL). The organic material was extracted with dichloromethane, dried (MgSO4), and concentrated to give an oil which was transformed to hydrochloride salt by adding 1 M solution of hydrogen chloride in diethyl ether. The white solid was collected by filtration: 1H NMR (DMSO-d) δ 1.14 (d, 3H, CH3), 2.94 (m, 2H, CH2), 3.52 (m, 1H, CH), 3.89 (s, 3H, OCH3), 7.38–8.06 (m, 6H, Ar—H), 8.19 (bs, NH3+); MS 216 (M+1). Analysis. Calcd. for C14H17NO.HCl.0.3 H2O: C, 65.39; H, 7.21; N, 5.56. Found: C, 65.16; H, 7.07; N, 5.42.

1. customthe solvent was removed
2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
3. washwashed with water (2×100 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. concentrationconcentrated
6. customto give a solid, which
7. temperaturecooled to 0° C
8. temperatureto warm to room temperature
9. stirringstirred for 2 h
10. temperatureby heating
11. temperatureat reflux for an additional 2 h
12. customExcess lithium aluminum hydride was consumed
13. additionby adding ethyl acetate (50 mL)
14. extractionThe organic material was extracted with dichloromethane
15. dry with materialdried (MgSO4)
16. concentrationconcentrated
17. customto give an oil which
18. filtrationThe white solid was collected by filtration