(6-Benzyloxy-4-methyl-indol-1-yl)-acetic acid tert-butyl ester → (6-Hydroxy-4-methyl-indol-1-yl)-acetic acid tert-butyl ester

HRID 915445Notes

Reaction equation

HRID 915445 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([CH3:25])[CH:13]=[C:14]([O:17]CC3C=CC=CC=3)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:26])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([CH3:25])[CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69280223(6-Benzyloxy-4-methyl-indol-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 69280225(6-Hydroxy-4-methyl-indol-1-yl)-acetic acid tert-butyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (6-benzyloxy-4-methyl-indol-1-yl)-acetic acid tert-butyl ester (140 mg, 0.4 mmol) in ethanol (14 ml) was hydrogenated over 10% palladium on charcoal (14 mg) at ambient temperature for 3 h. The catalyst was filtered off, the solvent evaporated under reduced pressure to give 100 mg (0.38 mmol, 96%) of the title compound as brown oil which was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-82e5786e519543298cfb33e45c014c0d
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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