反应详情

Propylamine (0.65 g) is dissolved in tetrahydrofuran (5 ml) and thereto is added pyridine (0.89 ml), followed by an addition dropwise of methyl adipoyl chloride (1.96 g) under ice-cooling and the mixture is stirred at room temperature for 1 hour. To the reaction mixture is added a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is dissolved in tetrahydrofuran (30 ml) and thereto is added sodium borohydride (1.93 g) at room temperature and the mixture is heated to 65° C. and thereto is added dropwise acetic acid (2.92 ml) over 1 hour and the mixture is stirred at the same temperature for 9 hours. To reaction mixture is added an ice-cooled dilute hydrochloric acid, and the mixture is stirred for 30 minutes and extracted with ethyl acetate, and the organic layer is washed with a mixed solution of a saturated aqueous sodium bicarbonate solution and a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is dissolved in methanol (5 ml) and thereto is added a 4N-hydrochloric acid in dioxane (7.5 mL) and the mixture is stirred at room temperature overnight. To the reaction mixture is added a saturated aqueous sodium bicarbonate solution and a saturated brine, and the mixture is extracted six times with ethyl acetate and the collected organic layer is dried over magnesium sulfate, and concentrated under reduced pressure to give methyl 6-propylamino-hexanoate (914 mg). MS (m/z): 188 [M+H]+

1. temperaturecooling
2. extractionthe mixture is extracted with ethyl acetate
3. washThe organic layer is washed with a saturated brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe resulting residue is dissolved in tetrahydrofuran (30 ml)
7. additionis added sodium borohydride (1.93 g) at room temperature
8. temperaturethe mixture is heated to 65° C.
9. additionis added dropwise acetic acid (2.92 ml) over 1 hour
10. stirringthe mixture is stirred at the same temperature for 9 hours
11. customTo reaction mixture
12. stirringthe mixture is stirred for 30 minutes
13. extractionextracted with ethyl acetate
14. washthe organic layer is washed with a mixed solution of a saturated aqueous sodium bicarbonate solution
15. dry with materiala saturated brine, dried over magnesium sulfate
16. concentrationconcentrated under reduced pressure
17. dissolutionThe resulting residue is dissolved in methanol (5 ml)
18. additionis added a 4N-hydrochloric acid in dioxane (7.5 mL)
19. stirringthe mixture is stirred at room temperature overnight
20. additionTo the reaction mixture is added a saturated aqueous sodium bicarbonate solution
21. extractiona saturated brine, and the mixture is extracted six times with ethyl acetate
22. dry with materialthe collected organic layer is dried over magnesium sulfate
23. concentrationconcentrated under reduced pressure