Water → 3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

HRID 1419167Notes

Reaction equation

HRID 1419167 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[C:22]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=O)=O)C1C=CC=CC=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].O>O1CCCC1.C(OCC)(=O)C>[CH3:15][N:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[CH2:22][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62649Sodium sulfate decahydrateHCID 18694411HCID 18694411, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 538704423-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of lithium aluminum hydride (1.71 g, 45.1 mmol, 4.5 eq) in anhydrous tetrahydrofuran (40 mL) at 0° C. was added dropwise a solution of the 3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-1H-indole (10.0 mmol) in anhydrous tetrahydrofuran (20 mL). The resulting reaction mixture was heated at reflux under nitrogen for 6 hours. The reaction mixture was cooled, and sodium sulfate decahydrate (50 g) was added very carefully portionwise, followed by water (1mL), and ethyl acetate (100 mL). The resulting mixture was stirred at room temperature under nitrogen for 24 hours. The reaction mixture was then filtered through Celite®, and the filtrate was evaporated under reduced pressure. The residue was then column chromatographed using silica gel (approximately 100 g) eluting with an appropriate solvent system to afford the desired 3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux under nitrogen for 6 hours
  4. temperatureThe reaction mixture was cooled
  5. filtrationThe reaction mixture was then filtered through Celite®
  6. customthe filtrate was evaporated under reduced pressure
  7. customcolumn chromatographed
  8. washeluting with an appropriate solvent system

Sources & evidence

ORD record
ord-fb6342ae76c74773a237fc7de0c67a7a
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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