HCID 54183315, compound → 1-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-indole-6-carboxylic acid

HRID 429645Notes

Reaction equation

HRID 429645 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19]CC3C=CC=CC=3)=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)=O.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 54183315HCID 54183315, compound

Product 1

HCID 183548491-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-indole-6-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

To a solution of benzyl 1-tert-butoxycarbonylindole-6-carboxylate (1.27 g) in 5.0% formic acid-methanol (20.0 ml) was added 10% palladium on carbon (1.27 g) and the mixture was stirred under nitrogen atmosphere at ambient temperature for 4 hours and stand overnight. The resulting solution was filtered through a bed of celite and the filtrate was concentrated in vacuo. The residue was diluted with chloroform and the solution was washed successively with water and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with ether:n-hexane (1:5) to give 1-tert-butoxycarbonylindoline-6-carboxylic acid (761 mg).

Workup

  1. waitstand overnight
  2. filtrationThe resulting solution was filtered through a bed of celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with chloroform
  5. washthe solution was washed successively with water and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ether:n-hexane (1:5)

Sources & evidence

ORD record
ord-3f74e378ea934785b818c08f32425a12
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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