反应详情

A solution of 2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-amine (2.50 g, 10.3 mmol) in 250 mL of 1,2-dichloroethane was treated with acetone (0.83 mL, 11.3 mmol), acetic acid (0.65 mL, 11.3 mmol) and sodium triacetoxyborohydride (2.39 g, 11.3 mL). After stirring overnight, additional acetone (5 mL), acetic acid (0.65 mL, 11.3 mmol) and sodium triacetoxyborohydride (2.39 g, 11.3 mL) were added. After 2 d, the reaction was carefully quenched by addition of saturated NaHCO3 solution. The layers were separated and the aqueous portion was extracted with additional CH2Cl2. The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure to give a brown oil. Some isopropylidene intermediate was still present, so the material was dissolved in 50 mL of MeOH and treated with NaBH4 (1.0 g). After 2 h, the reaction was quenched by the addition of H2O and the reaction mixture was concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 solution and CH2Cl2. The layers were separated and the organic portion was washed with saturated NaHCO3, H2O and brine. The organic portion was dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 4% MeOH/CHCl3) gave N-(2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (0.98 g) as a brown oil.

1. waitAfter 2 d
2. customthe reaction was carefully quenched by addition of saturated NaHCO3 solution
3. customThe layers were separated
4. extractionthe aqueous portion was extracted with additional CH2Cl2
5. washThe combined organic layers were washed with H2O and brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customto give a brown oil
9. waitAfter 2 h
10. customthe reaction was quenched by the addition of H2O
11. concentrationthe reaction mixture was concentrated under reduced pressure
12. customThe residue was partitioned between saturated NaHCO3 solution and CH2Cl2
13. customThe layers were separated
14. washthe organic portion was washed with saturated NaHCO3, H2O and brine
15. dry with materialThe organic portion was dried over Na2SO4
16. filtrationfiltered
17. concentrationconcentrated under reduced pressure