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 268786Notes

Reaction equation

HRID 268786 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-5cef03c1bb904c5eac4b9a04f46b1568
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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