3-(Allyl-benzyl-carbamoyl)-but-3-enoic acid methyl ester → (1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid methyl ester

HRID 2240577Notes

Reaction equation

HRID 2240577 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]([C:7](=[O:19])[N:8]([CH2:16][CH:17]=C)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=C>C(Cl)Cl.[Ru]>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[C:7](=[O:19])[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:16][CH:17]=1

Participants

4

Reactant 1

HCID 574434143-(Allyl-benzyl-carbamoyl)-but-3-enoic acid methyl ester

Product 1

HCID 57443415(1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid methyl esterYield 85.7%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

234 mg of 3-(allyl-benzyl-carbamoyl)-but-3-enoic acid methyl ester (o) (0.1 mM) prepared by the above Step 1 was added to the catalyst solution containing 36 mg of Grubb's (I) catalyst (0.04 mM) such as ruthenium dissolved in CH2Cl2 under Ar atmosphere. Then the mixture was stirred for 24 hrs at room temperature, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with EtOAc and hexanes (1:2) as an eluant to give 180 mg of (1-benzyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid methyl ester (p) (yield: 85%).

Workup

  1. additionwas added to the catalyst solution
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resultant was purified by Silica gel column chromatography with a solvent mixture
  5. additionmixed with EtOAc and hexanes (1:2) as an eluant

Sources & evidence

ORD record
ord-95d7c60486be49819875dd33df015d75
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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