(Z)-2-Ethoxy-3-(1H-indol-5-yl)-acrylic Acid Ethyl Ester → Rac-2-ethoxy-3-(1h-indol-5-yl)-propionic acid ethyl ester

HRID 2181183Notes

Reaction equation

HRID 2181183 reaction equation
[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[O:16][CH2:17][CH3:18])=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)[CH3:2].[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)[CH3:2]

Participants

5

Reactant 2

HCID 53309301(Z)-2-Ethoxy-3-(1H-indol-5-yl)-acrylic Acid Ethyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 69563293Rac-2-ethoxy-3-(1h-indol-5-yl)-propionic acid ethyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 9.7 g of (Z)-2-ethoxy-3-(1H-indol-5-yl)-acrylic acid ethyl ester in 100 ml of EtOH and 1.0 g of Pd/C (10%) was hydrogenated at 22° C. for 2 h after which time hydrogen uptake ceased. The suspension was filtered, the filtrate evaporated and the residue chromatographed on silica (n-hexane/AcOEt, 2:1) to give 8.7 g of the title compound as a white solid. MS: (M)+ 261.2.

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated
  3. customthe residue chromatographed on silica (n-hexane/AcOEt, 2:1)

Sources & evidence

ORD record
ord-5b008fc36b014dc5aa3d03d8d2b8482a
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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