Ethyl 2-(5-benzyloxyindolyl)cyclopropanecarboxylate → Ethyl 2-(5-hydroxyindolyl)cyclopropanecarboxylate

HRID 1295108Notes

Reaction equation

HRID 1295108 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH:18]1[CH2:20][CH:19]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12]2)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH:18]1[CH2:20][CH:19]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12]2

Participants

4

Reactant 1

HCID 22570370Ethyl 2-(5-benzyloxyindolyl)cyclopropanecarboxylate

Product 1

HCID 22570391Ethyl 2-(5-hydroxyindolyl)cyclopropanecarboxylateYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 2-(5-benzyloxyindolyl)cyclopropanecarboxylate(1.75 g, 0.0052 mol), as prepared in the preceding step, was added under argon to a suspension of 10% of palladium(0) on carbon (0.50 g) in methanol (50 mL). The reaction was carried out under H2 atmosphere for a period of 6 h. Filtration of the reaction over Celite and evaporation of the filtrate yielded the title compound (1.27 g, 99%). 1H NMR (400 MHz, CDCl3) δ 1.32 (t, 3H, J=7.1 Hz), 1.60 (m, 1H), 1.72 (m, 1H), 2.13 (m, 1H), 3.77 (m, 1H), 4.25 (q, 2H, J=7.1 Hz), 6.29 (d, 1H, J=3.0 Hz), 6.81 (d, 1H, J=8.3 Hz), 7.00 (m, 2H), 7.27 (m, 1H)

Workup

  1. filtrationFiltration of the reaction
  2. customover Celite and evaporation of the filtrate

Sources & evidence

ORD record
ord-daadc311939b4787a73b4c0168092f57
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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