1-tert-butyl 2-ethyl 4-(benzyloxy)-1H-indole-1,2-dicarboxylate → 1-tert-butyl 2-ethyl 4-hydroxy-1H-indole-1,2-dicarboxylate

HRID 1929191Notes

Reaction equation

HRID 1929191 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15]CC1C=CC=CC=1)[CH:11]=[CH:10][CH:9]=2)=[O:5]>C(OCC)(=O)C.[Pd]>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C:8]2[C:13]([CH:14]=1)=[C:12]([OH:15])[CH:11]=[CH:10][CH:9]=2)=[O:5]

Participants

4

Reactant 1

HCID 591526751-tert-butyl 2-ethyl 4-(benzyloxy)-1H-indole-1,2-dicarboxylate

Product 1

HCID 596001381-tert-butyl 2-ethyl 4-hydroxy-1H-indole-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

158 (8 g, 20 mmol) is dissolved in 80 ml of ethyl acetate and, after addition of 5% Pd—C (700 mg), the mixture is hydrogenated at room temperature for 7 hours. The mixture is filtrated over celite to remove the catalyst and evaporated. The solid is suspended in ether/hexane and filtered.

Workup

  1. filtrationThe mixture is filtrated over celite
  2. customto remove the catalyst
  3. customevaporated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a114fd81fb6d4b1f84d5b957dedd5af2
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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