反应详情

tert-Butyl (2S)-2-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (2.54 g, 6.77 mmol) was dissolved in 2.2 M HCl in EtOH (50 mL) and the solution was heated to reflux for 15 minutes. N2 was bubbled through the reaction for 15 minutes, and the remaining volatiles were removed under reduced pressure. The resulting material was partitioned between dichloromethane and water. The organic layer was discarded and the aqueous layer was treated with concentrated NH4OH solution to adjust to pH 11. The aqueous layer was extracted with dichloromethane (3×100 mL), and the combined organic layers were washed with brine. Triethylamine (4 mL) was then added to the solution and it was stirred at ambient temperature overnight. The reaction was washed successively with water (2×100 mL) and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to give an orange foam. Chromatography (SiO2, 20-50% CMA/CHCl3) gave (11S)-11-methyl-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline (1.06 g) as an orange foam.

1. temperaturethe solution was heated
2. temperatureto reflux for 15 minutes
3. customN2 was bubbled through the reaction for 15 minutes
4. customthe remaining volatiles were removed under reduced pressure
5. customThe resulting material was partitioned between dichloromethane and water
6. additionthe aqueous layer was treated with concentrated NH4OH solution
7. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
8. washthe combined organic layers were washed with brine
9. additionTriethylamine (4 mL) was then added to the solution and it
10. washThe reaction was washed successively with water (2×100 mL) and brine
11. dry with materialThe organic layer was dried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customto give an orange foam