methyl 3-[2-((E)-2-benzyloxycarbonylethenyl)pyrrol-1-yl)benzoate → Methyl 3-[2-(2-carboxyethyl)pyrrol-1-yl]benzoate

HRID 399831Notes

Reaction equation

HRID 399831 reaction equation
C([O:8][C:9](/[CH:11]=[CH:12]/[C:13]1[N:14]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])[CH:15]=[CH:16][CH:17]=1)=[O:10])C1C=CC=CC=1>[Pd].CO>[C:9]([CH2:11][CH2:12][C:13]1[N:14]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])[CH:15]=[CH:16][CH:17]=1)([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 18945360methyl 3-[2-((E)-2-benzyloxycarbonylethenyl)pyrrol-1-yl)benzoate

Product 1

HCID 18945413Methyl 3-[2-(2-carboxyethyl)pyrrol-1-yl]benzoateYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (0.25 g) was added to the solution of methyl 3-[2-((E)-2-benzyloxycarbonylethenyl)pyrrol-1-yl]benzoate (2.5 g) in methanol (50 ml) and the mixture was subjected to catalytic reduction at the ambient temperature under atmospheric pressure. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 3-[2-(2-carboxyethyl)pyrrol-1-yl]benzoate (1.02 g).

Workup

  1. customwas subjected to catalytic reduction at the ambient temperature under atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-6872e3f0a2d4498ab9e24f043e296fe2
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…