反应详情

To a solution of tert-butyl 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}-4-hydroxypiperidine-1-carboxylate (prepared as described in Part E of Example 4, 14.94 g, 33.91 mmol) in ethanol (170 mL) was added a solution of HCl in ethanol (2.7 M, 31 mL, 84.7 mmol). The solution was heated at reflux for 1 h, during which time a precipitate formed. The mixture was allowed to cool to rt and the volatiles were removed under reduced pressure. To the residue was added water (400 mL) followed by 50% aqueous NaOH until the pH=10. The solution was extracted with dichloromethane (3×100 mL). The aqueous layer was treated with 50% aqueous NaOH until the pH=12, then was extracted with dichloromethane (2×100 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was triturated with hot ethyl acetate and the remaining solid was isolated by filtration to afford 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidin-4-ol (7.0 g, 61%) as an off-white powder.

1. temperatureThe solution was heated
2. temperatureat reflux for 1 h, during which time a precipitate
3. customformed
4. customthe volatiles were removed under reduced pressure
5. additionTo the residue was added water (400 mL)
6. extractionThe solution was extracted with dichloromethane (3×100 mL)
7. additionThe aqueous layer was treated with 50% aqueous NaOH until the pH=12
8. extractionwas extracted with dichloromethane (2×100 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe resulting solid was triturated with hot ethyl acetate
13. customthe remaining solid was isolated by filtration