3-(5-Benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester → 3-(5-Hydroxy-indol-1-yl)-3-phenyl-propionic acid ethyl ester

HRID 1295144

Reaction equation

HRID 1295144 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[C:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22]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]>[Pd].CO>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([OH:22])=[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]

Participants

4

Reactant 1

HCID 674277863-(5-Benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 668214783-(5-Hydroxy-indol-1-yl)-3-phenyl-propionic acid ethyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(5-benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester (1.94 g, 4.89 mmol) and palladium on carbon [10% w/w] (60 mg) in methanol (25 mL) was stirred under hydrogen atmosphere for 24 h. After removal of the catalyst by filtration, the crude product was purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1) to give the title compound in 96% yield. 1H NMR (CDCl3) δ 7.10–7.30 (m, 7H), 6.99 (d, J=2.4 Hz, 1H), 6.69 (dd, J=2.4 and 8.7 Hz, 1H), 6.39 (d, J=3.2 Hz, 1H), 5.99 (t, J=7.6 Hz, 1H), 5.31 (br, 1H), 4.03 (q, J=7.2 Hz, 2H), 3.26 (m, 2H), 1.08 (t, J=7.2 Hz, 3H). 13C NMR (CDCl3) δ 170.4, 149.7, 139.8, 131.5, 129.3, 128.8, 127.9, 126.2, 125.8, 111.6, 110.6, 105.2, 101.4, 61.1, 56.2, 40.4, 13.9. Mass Spectrum (LCMS, ESI) calculated for C19H20NO3 310.1 (M+H); found 310.1.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe crude product was purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-449305433538438f85ec024d6cce68ae
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Linked notes

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