Water → 3-(pyrrolidin-2-ylmethyl)-1H-indole

HRID 1419168Notes

Reaction equation

HRID 1419168 reaction equation
[BH4-].[Li+].[NH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[C:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].O>O1CCCC1.C(OCC)(=O)C>[NH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62649Sodium sulfate decahydrateHCID 4148881Lithium borohydrideHCID 545453013-(pyrrolidine-2-carbonyl)-1H-indole

Product 1

HCID 185089963-(pyrrolidin-2-ylmethyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of lithium borohydride (0.33 g, 15.2 mmol, 3.0 eq) in anhydrous tetrahydrofuran (10 mL) under nitrogen was added dropwise a solution of the 3-(pyrrolidin-2-ylcarbonyl)-1H-indole (10 mmol) in anhydrous tetrahydrofuran (40 mL). The resulting reaction solution was heated at reflux under nitrogen for a time depending on the substrate. The reaction was then cooled, and sodium sulfate decahydrate (approximately 25 g) was added slowly with caution, followed by water (1 mL), and ethyl acetate (50 mL). The resulting reaction mixture was stirred at room temperature under nitrogen for 4 hours. Then the reaction mixture was filtered through Celite®, and the filtrate was evaporated under reduced pressure. The residue was column chromatographed using silica gel (approximately 200 g) eluting with an appropriate solvent system to afford the appropriate 3-(pyrrolidin-2-ylmethyl)-1H-indole.

Workup

  1. customThe resulting reaction solution
  2. temperaturewas heated
  3. temperatureat reflux under nitrogen for a time
  4. temperatureThe reaction was then cooled
  5. customThe resulting reaction mixture
  6. filtrationThen the reaction mixture was filtered through Celite®
  7. customthe filtrate was evaporated under reduced pressure
  8. customchromatographed
  9. washeluting with an appropriate solvent system

Sources & evidence

ORD record
ord-2ace6b3f8d9b452baa06dc214ba7e033
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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