Benzyl 4-(3-nonyloxycarbonyl-1-indolyl)butyrate → 4-(3-Nonyloxycarbonyl-1-indolyl)butyric acid

HRID 260866Notes

Reaction equation

HRID 260866 reaction equation
[CH2:1]([O:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][CH2:23][CH2:24][C:25]([O:27]CC2C=CC=CC=2)=[O:26])[CH:14]=1)=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>CO.O1CCOCC1.[C].[Pd]>[CH2:1]([O:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:14]=1)=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 1

HCID 22400555Benzyl 4-(3-nonyloxycarbonyl-1-indolyl)butyrate

Product 1

HCID 224005334-(3-Nonyloxycarbonyl-1-indolyl)butyric acidYield 82,978.297%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of benzyl 4-(3-nonyloxycarbonyl-1-indolyl)butyrate (368 mg) obtained in Ex. 62 and 10% palladium carbon (0.10 g) in methanol and 1,4-dioxane was stirred at room temperature for 2 hours under a hydrogen atmosphere at 3 atm. Removal of the catalyst and evaporation of the solvent afforded 4-(3-nonyloxycarbonyl-1-indolyl)butyric acid (246 g) as a solid.

Workup

  1. customobtained in Ex
  2. customRemoval of the catalyst and evaporation of the solvent

Sources & evidence

ORD record
ord-18fefe880029477e93f85c894aba0119
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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