Methyl 3-(5-benzyloxyindolyl)propanoate → methyl 3-(5-hydroxy-1H-indol-2-yl)propanoate

HRID 1295112Notes

Reaction equation

HRID 1295112 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:12]2)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:12]2

Participants

4

Reactant 1

HCID 22570323Methyl 3-(5-benzyloxyindolyl)propanoate

Product 1

HCID 22570384methyl 3-(5-hydroxy-1H-indol-2-yl)propanoateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 3-(5-benzyloxyindolyl)propanoate (1.1 g, 3.56 mmol), as prepared in the preceding step, 10% palladium(0) on carbon (100 mg) in ethanol was stirred under hydrogen for 3 h. The catalyst was removed by filtration, the filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (1–5% ethyl acetate in methylene chloride) to give the title compound as a pale yellow oil (700 mg, 90%). 1H-NMR (400 M Hz, CDCl3) δ 7.18 (d, J=8.8 Hz, 1H), 7.08 (d, J=3.1 Hz, 1H), 7.02 (d, J=3.2 Hz, 1H), 6.77 (dd, J=8.8, 2.5 Hz, 1H), 6.34 (d, J=3.1 Hz, 1H), 4.75 (s, 1H), 4.40 (t, J=6.9 Hz, 2H), 3.66 (s, 3H), 2.81 (t, J=6.9 Hz, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue was purified by flash column chromatography (1–5% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-8329f724f4734f20a6b88b102ae3876d
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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