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

HRID 1790909Notes

Reaction equation

HRID 1790909 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-96215529b7e347b4ac76b99153d11260
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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