(5-Benzyloxyindole-1-yl)acetic acid methyl ester → methyl (5-hydroxy-1H-indol-1-yl)acetate

HRID 1296060Notes

Reaction equation

HRID 1296060 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14]CC3C=CC=CC=3)=[CH:11][CH:12]=2)[CH:7]=[CH:6]1>C(OCC)(=O)C.C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:22])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

4

Reactant 1

HCID 20770836(5-Benzyloxyindole-1-yl)acetic acid methyl ester

Product 1

HCID 20770839methyl (5-hydroxy-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Compound 72A (18.9 g, 64 mmol) was dissolved in 100 ml 1:1 ethyl acetate/ethanol. 200 mg 10% Pd/C was added followed by purging with hydrogen. The reaction was stirred vigorously under balloon pressure for 16 h. The reaction was filtered through Celite® and concentrated to an oil which was filtered through 0.45 uM filter to give a pale yellow oil which crystallized on standing. MS m/z 206 (M+1).

Workup

  1. customby purging with hydrogen
  2. filtrationThe reaction was filtered through Celite®
  3. concentrationconcentrated to an oil which
  4. filtrationwas filtered through 0.45 uM
  5. filtrationfilter
  6. customto give a pale yellow oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-20780514517043c3b197da62948ccf99
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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