(6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester → Methyl 2-(6-hydroxy-1H-indol-3-yl)acetate

HRID 490685

Reaction equation

HRID 490685 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]CC3C=CC=CC=3)=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=O>O1CCOCC1.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[NH:8][CH:7]=1

Participants

4

Reactant 1

HCID 34181007(6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester

Product 1

HCID 57675479Methyl 2-(6-hydroxy-1H-indol-3-yl)acetateYield 62.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (6-benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester (1.45 g, 4.7 mmol) and Pd/C (10%, 0.9 g) in dioxane (38 mL) is degassed and filled with nitrogen for three times, then a solution of NaH2PO2 (6 g) in water (5 mL) is added dropwise at 100° C. The reaction mixture is heated overnight, filtered through celite and concentrated. The residue is taken into ethyl acetate, washed with water and brine, dried over sodium sulfate. Concentration and column chromatography on silica gel yields the title compound (600 mg).

Workup

  1. customis degassed
  2. additionfilled with nitrogen for three times
  3. additiona solution of NaH2PO2 (6 g) in water (5 mL) is added dropwise at 100° C
  4. temperatureThe reaction mixture is heated overnight
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationConcentration and column chromatography on silica gel

Sources & evidence

ORD record
ord-4b5e3dd0e12646ada240bc91d7245118
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Linked notes

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