6-tert-Butyl indole-1-carboxylic acid tert-butyl ester → 1h-Indole-1-carboxylic acid,6-(1,1-dimethylethyl)-2,3-dihydro-,1,1-dimethylethyl ester

HRID 1859549Notes

Reaction equation

HRID 1859549 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 539221666-tert-Butyl indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 540929591h-Indole-1-carboxylic acid,6-(1,1-dimethylethyl)-2,3-dihydro-,1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6-tert-Butyl indole-1-carboxylic acid tert-butyl ester (prepared in Example GG; 13.0 g, 48 mmol) was taken up in 500 mL of AcOH. 20% Pd/C (2 g) was added, and the mixture was shaken under a hydrogen atmosphere of 50 psi. The catalyst was filtered, and the filtrate was concentrated. The residue was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, and dried (MgSO4). Concentration gave the title compound which was used without purification in the next step.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3 solution and brine
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration

Sources & evidence

ORD record
ord-130139676f584023bc7d368dbcf724be
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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