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

HRID 1925491Notes

Reaction equation

HRID 1925491 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C(C)C)(C(C)C)[N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:32][C@H:33]([NH:37][CH2:38][CH2:39][CH3:40])[CH2:34][CH2:35][CH3:36])=[CH:24]1)(C)C.C(=O)([O-])O.[Na+].C(OCC)C>O1CCCC1>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:32][C@H:33]([NH:37][CH2:38][CH2:39][CH3:40])[CH2:34][CH2:35][CH3:36])=[CH:24]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 67426035(R)-1-(1-triisopropylsilylindole-3-yl)-2-propylaminopentane

Product 1

HCID 67426163(R)-1-(3-indolyl)-2-propylaminopentaneYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-73d355927b0c44168c4502ed3459cba4
Source dataset
uspto-grants-2012_05
Patent number
US08178686B2

Reaction notes

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