反应详情

To a solution of 4-(dimethylaminocarbonyloxy)-3-(methoxy)benzaldehyde (1.02 g) in 1,2-dichloroethane (16 ml) was added 6,7-dimethoxytetrahydroisoquinoline(0.97 g) and sodium triacetoxyborohydride (1.35 g), with stirring. The mixture was stirred at ambient temperature for 1 hr, poured onto ice/sodium carbonate solution and extracted with ethyl acetate. The extracts were washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and flash column chromatographed (silica gel), eluting with dichloromethane, 1% and 2% methanol dichloromethane. The appropriate fractions were collected and concentrated to give 0.92 g (50.3%/o) of product. Recrystallization from ethyl acetate gave the analytical sample, mp 126-128° C.

1. stirringThe mixture was stirred at ambient temperature for 1 hr
2. additionpoured onto ice/sodium carbonate solution
3. extractionextracted with ethyl acetate
4. washThe extracts were washed with water, saturated sodium chloride solution
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. dissolutionThe residue was dissolved in dichloromethane
9. customflash column chromatographed (silica gel)
10. washeluting with dichloromethane, 1% and 2% methanol dichloromethane
11. customThe appropriate fractions were collected
12. concentrationconcentrated
13. customto give 0.92 g (50.3%/o) of product
14. customRecrystallization from ethyl acetate
15. customgave the analytical sample, mp 126-128° C.