Benzyl 1-(4-ethoxycarbonylbutyl)indole-2-carboxylate → HCID 19085099, compound

HRID 963091Notes

Reaction equation

HRID 963091 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:19]([O:21]CC1C=CC=CC=1)=[O:20])=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:19]([OH:21])=[O:20])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 19085282Benzyl 1-(4-ethoxycarbonylbutyl)indole-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19085099HCID 19085099, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 1-(4-ethoxycarbonylbutyl)indole-2-carboxylate (12.44 g) was dissolved in ethanol (120 ml). The mixture was subjected to catalytic reduction by blowing a hydrogen gas in the presence of 10% palladium/carbon. The reaction mixture was filtered through Celite to remove catalyst. The solvent was evaporated, and the residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate and hexane as an eluent to give 2.19 g of 1-(4-ethoxycarbonylbutyl)indole-2-carboxylic acid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customto remove catalyst
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f18e97e96e29477393439096436b1a8f
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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