Diethyl Ether → (R)-1-(3-indolyl)-2-propylaminopentane

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Reaction Steps

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.

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