反应详情

Tetra-n-butylammonium fluoride (9.64 g) was added to a solution of (R)-1-(1-triisopropylsilylindole-3-yl)-2-propylaminopentane (9.85 g) in tetrahydrofuran (45 mL) under stirring at room temperature and then stirred at room temperature for 50 minutes. A saturated aqueous sodium hydrogen carbonate solution (20 mL) and diethyl ether (40 mL) were added to the resulting solution. The organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to column chromatography (NH-DM1020, AcOEt/Hexane=1/6). An aqueous 1 mol/L hydrochloric acid solution (100 mL) and diethyl ether (100 mL) were added to the resulting oil, and then the organic layer was extracted with an aqueous 1 mol/L hydrochloric acid solution. The aqueous layers were combined and washed with diethyl ether (30 mL). The aqueous layer was made basic with an aqueous 1 mol/L sodium hydroxide solution and extracted twice with diethyl ether (60 mL). The organic layers were combined and washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give (R)-1-(3-indolyl)-2-propylaminopentane (5.78 g, 96% yield) as a light orange oil.

1. stirringstirred at room temperature for 50 minutes
2. customThe organic layer was separated
3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. additionAn aqueous 1 mol/L hydrochloric acid solution (100 mL) and diethyl ether (100 mL) were added to the resulting oil
7. extractionthe organic layer was extracted with an aqueous 1 mol/L hydrochloric acid solution
8. washwashed with diethyl ether (30 mL)
9. extractionextracted twice with diethyl ether (60 mL)
10. washwashed with a saturated aqueous sodium hydrogen carbonate solution
11. dry with materialdried over anhydrous sodium sulfate
12. concentrationconcentrated under reduced pressure