Water → [5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-yl]-methanol

HRID 49059Notes

Reaction equation

HRID 49059 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][CH2:16][C:17](=O)[N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[CH:10][CH:9]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:18]1([CH2:17][CH2:16][CH2:15][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([CH2:4][OH:3])=[CH:14]3)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 695868775-(3-oxo-3-pyrrolidin-1-yl-propyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 22042173[5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-yl]-methanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-oxo-3-pyrrolidin-1-yl-propyl)-1H-indole-2-carboxylic acid ethyl ester (1.5 g, 4.8 mmol) in 100 mL of tetrahydrofuran, lithium aluminum hydride powder (728 mg, 19.2 mmol) was added. The mixture was stirred under nitrogen at room temperature for 2 hour. To the reaction mixture was added water (0.75 mL), 15% sodium hydroxide (0.75 mL) and water (0.75 mL). It was then filtered through a pad of celite and the filtrate was concentrated. The residue was washed with ethyl acetate to give 960 mg (78%) of [5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-yl]-methanol.

Workup

  1. filtrationIt was then filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-a211efdf2c064b5aa629326e25f9e9c3
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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