Aluminium lithium hydride → HCID 44292367, compound

HRID 1870963Notes

Reaction equation

HRID 1870963 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[C:22]([C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([CH3:33])[CH:31]=2)[NH:26][CH:25]=1)=O)=O)C1C=CC=CC=1>C1COCC1>[NH3:17].[CH3:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:22][C@H:18]1[CH2:19][CH2:20][CH2:21][N:17]1[CH3:15]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53831906HCID 53831906, compound

Product 2

HCID 222AmmoniaYield 6%HCID 44292367HCID 44292367, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LAH (39 mL, 1 M in THF, 39 mmol) was added slowly to a cooled (0° C.) solution of (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl]-5-methyl-1H-indole (Example 1b, 9.5 mmol) in THF (100 mL). Once the addition was completed, the reaction mixture was stirred at reflux overnight prior to quenching with sodium sulfate decahydrate. The product was taken into ethyl acetate, filtered to remove the solid residue, and the solvent was removed in vacuo. The product was taken into ethyl acetate, filtered to remove the solid residue, and the solvent was removed in vacuo. Flash chromatography (silica gel, 6% 2M methanolic ammonia in dichloromethane) yielded (R)-5-methyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole (52%; yellow oil; HRMS-FAB+ for C15H20N2 : calculated MH+ :229.1705; found MH+ :229.1706).

Workup

  1. additionOnce the addition
  2. temperatureat reflux overnight
  3. customto quenching with sodium sulfate decahydrate
  4. filtrationfiltered
  5. customto remove the solid residue
  6. customthe solvent was removed in vacuo
  7. filtrationfiltered
  8. customto remove the solid residue
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-879056ea1b264f3e969c167b56d8bfad
Source dataset
uspto-grants-2000_08
Patent number
US06100291

Reaction notes

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