HCID 66819378, compound → 3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester

HRID 23993Notes

Reaction equation

HRID 23993 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH:5]=[C:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25]CC3C=CC=CC=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][OH:25])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 66819378HCID 66819378, compound

Product 1

HCID 674283203-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

3-[-5-(2-benzyloxy-ethoxy)-indol-1-yl]-3-phenyl-acrylic acid ethyl ester (2.5 g, 5.6 mmol) was dissolved in 70% ethyl acetate/methanol (50 mL) and added under an argon atmosphere to a suspension of 10% palladium on carbon [10% w/w] (3.0 g) in the same solvent (50 mL). The reaction was placed in a Parr Hydrogenator for 6 h. The reaction was filtered through celite and the solvent was evaporated under vacuum. Purification of the crude mixture via column chromatography with silica gel, eluting with hexane/ethyl acetate gave the title compound (80% yield). 1H NMR (CDCl3), δ 7.14-7.32 (m, 7H), 6.82 (dd, 1H, J=2.3, 8.8 Hz), 6.45 (d, 1H, J=3.0 Hz), 6.07 (d, 1H, J=2.1 Hz), 6.01 (t, 1H, J=7.4 Hz), 4.03 (m, 4H), 3.91 (m, 2H), 3.27 (m, 2H), 1.06 (t, 3H, J=7.2 Hz).

Workup

  1. filtrationThe reaction was filtered through celite
  2. customthe solvent was evaporated under vacuum
  3. customPurification of the crude mixture via column chromatography with silica gel
  4. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-6d4c6e9923b748e1996d26d298abffb3
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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