3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester → 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

HRID 268817Notes

Reaction equation

HRID 268817 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[C:6]([C:13]1[CH:21]=[C:20]([O:22][CH3:23])[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.C(Cl)Cl.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]([C:13]1[CH:21]=[C:20]([O:22][CH3:23])[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 673560903-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 598317283-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

Degoussa-type catalyst (50% Pd/C, 45 mg) was added to a solution of 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester CXVI (0.40 g, 1.2 mmol) in EtOH/DCM (6/1, 40 ml). The resulting mixture was hydrogenated in a Parr apparatus at 50 psi of H2 for 16 hours, filtered through celite, and the filter cake was washed with EtOH and DCM. The filtrate was concentrated, affording 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester CXVII.

Workup

  1. filtrationfiltered through celite
  2. washthe filter cake was washed with EtOH and DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d8cc945264c744349df2f2b23b50c095
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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