Aluminium lithium hydride → [5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-methanol

HRID 49050Notes

Reaction equation

HRID 49050 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH2:22][C:23]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=O)=[CH:16][CH:15]=2)=O)C>O1CCCC1>[N:25]1([CH2:23][CH2:22][O:21][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]([CH2:10][OH:9])=[CH:20]3)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 695873915-(2-morpholin-4-yl-2-oxo-ethoxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 22042178[5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-methanolYield 105.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.46 g, 12 mmol) was added-5-(2-morpholin-4-yl-2-oxo-ethoxy)-1H-indole-2-carboxylic acid ethyl ester (0.8 g, 2.4 mmol) in tetrahydrofuran (50 mL). The mixture was stirred at room temperature for 16 hours and cooled to 0° C. It was then quenched with water (4.6 mL), 15% sodium hydroxide (4.6 mL) and water (4.6 mL). The precipitate was filtered off and the filtrate was concentrated to give 0.7 g of [5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-methanol.

Workup

  1. temperaturecooled to 0° C
  2. customIt was then quenched with water (4.6 mL), 15% sodium hydroxide (4.6 mL) and water (4.6 mL)
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0add60555478466db0b8342da248ecd2
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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