HCID 21717241, compound → 1,1-Dimethylethyl 2-(2,3-dihydro-2-oxo-1H-indol-6-yl)-1-pyrrolidinecarboxylate

HRID 1386353Notes

Reaction equation

HRID 1386353 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][C:18](=[O:22])[NH:19]2)=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:21]=[C:20]2[C:16]([CH2:17][C:18](=[O:22])[NH:19]2)=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 21717241HCID 21717241, compound

Product 1

HCID 217173071,1-Dimethylethyl 2-(2,3-dihydro-2-oxo-1H-indol-6-yl)-1-pyrrolidinecarboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-(1-t-butoxycarbonylpyrrol-2-yl)oxindole (560 mg, 1.9 mmol), (prepared as described for the starting material in Example 63), and 10% palladium-on-charcoal catalyst (50 mg) in ethyl acetate (30 ml) was stirred under hydrogen at 1 atmosphere pressure for 3 days. The catalyst was removed by filtration through diatomaceous earth, the solvent was removed by evaporation and the residue triturated with ether/isohexanes (1/5) and collected by filtration to give 6-(1-t-butoxycarbonylpyrrolidin-2-yl)oxindole (480 mg, 85%) as a pale yellow solid.

Workup

  1. custom(prepared
  2. customThe catalyst was removed by filtration through diatomaceous earth
  3. customthe solvent was removed by evaporation
  4. customthe residue triturated with ether/isohexanes (1/5)
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-98fa233355624ebbb8e916b9d2ef6c6e
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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