4-[3-(3,7-Dimethyl-6-octenoyl)-1-indolyl]butyric acid → 4-[3-(3,7-Dimethyloctanoyl)-1-indolyl]butyric acid

HRID 260849Notes

Reaction equation

HRID 260849 reaction equation
[CH3:1][CH:2]([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH2:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:7]=1)=[O:5]>CO.[C].[Pd]>[CH3:1][CH:2]([CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:7]=1)=[O:5]

Participants

4

Reactant 1

HCID 224005274-[3-(3,7-Dimethyl-6-octenoyl)-1-indolyl]butyric acid

Product 1

HCID 224004664-[3-(3,7-Dimethyloctanoyl)-1-indolyl]butyric acidYield 52.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[3-(3,7-dimethyl-6-octenoyl)-1-indolyl]butyric acid (267 mg) obtained in Ex. 30 and 10% palladium carbon (80 mg) in methanol was stirred at room temperature for 3 hours under a hydrogen atmosphere at 3 atm. The catalyst was removed and the solvent was evaporated. The residue was chromatographed on a silica gel column (3-10% methanol in chloroform as an eluent) to give 4-[3-(3,7-dimethyloctanoyl)-1-indolyl]butyric acid (142 mg) as an oil.

Workup

  1. customobtained in Ex
  2. customThe catalyst was removed
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed on a silica gel column (3-10% methanol in chloroform as an eluent)

Sources & evidence

ORD record
ord-54ba5494753240d0a0f0323012d04161
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

Loading…