Water → [1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]methanol

HRID 349892Notes

Reaction equation

HRID 349892 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH2:15][CH2:16][O:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:25]([C:34](OC)=[O:35])=[CH:24]2)=[CH:20][CH:19]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.O>O1CCCC1>[CH3:7][N:8]([CH2:15][CH2:16][O:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[CH:27]=[C:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:25]([CH2:34][OH:35])=[CH:24]2)=[CH:20][CH:19]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 69421923methyl 1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolecarboxylate

Product 1

HCID 69427226[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]methanolYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (305 mg) was added to a solution of methyl 1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolecarboxylate (1.78 g) in tetrahydrofuran (40 ml) at 0° C., and the mixture was stirred at room temperature for 6 hours. After water was added to the reaction mixture, the precipitate was removed by filtration and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and [1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]methanol (1.45 g, yield: 87%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. customthe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-103b233052c841e59fd95faa4f6b455b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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