Ammonium formate → N-Boc-5-Hydroxyindole

HRID 605140Notes

Reaction equation

HRID 605140 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10663688tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate

Product 1

HCID 22596220N-Boc-5-HydroxyindoleYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of Example 93A (680 mg, 2.103 mmol) in ethanol (20 mL) was treated with 10% palladium-on-carbon (68 mg) and ammonium formate (265 mg, 4.205 mmol), and stirred at room temperature under a nitrogen atmosphere for 1 hour. The reaction was filtered through a 0.45 μ PTFE membrane and the catalyst washed with methanol. The filtrate was concentrated by rotary evaporation under vacuum and the residue taken up in ethyl acetate (50 mL), washed with water (2×25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a white solid (475 mg, 96%).

Workup

  1. filtrationThe reaction was filtered through a 0.45 μ PTFE membrane
  2. washthe catalyst washed with methanol
  3. concentrationThe filtrate was concentrated by rotary evaporation under vacuum
  4. washwashed with water (2×25 mL) and brine (25 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-eed772ab45744478b9d34ea37ba8c9fb
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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