3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester → 3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

HRID 1716657Notes

Reaction equation

HRID 1716657 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[C:6]([C:13]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]([C:13]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 673557843-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 598318913-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester XLVIII (37 mg, 0.115 mmol) in EtOH (4 ml) and a catalytic amount of Degoussa-type catalyst Pd/C wet (10%) was subjected to hydrogenation conditions in a Parr apparatus at 60 psi of H2 for 20 hours. The reaction mixture was filtered through celite with MeOH. The filtrate was concentrated and subjected to the same hydrogenation conditions for 24 hours to provide 3-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester XLIX (37 mg) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite with MeOH
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1adee339c3664034908467378546d3a3
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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