HCID 57443422, compound → HCID 67453428, compound

HRID 2240588Notes

Reaction equation

HRID 2240588 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][C:6]([C:8](=[O:23])[N:9]([CH2:20][CH:21]=C)[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=C>[Ru].C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][C:6]1[C:8](=[O:23])[N:9]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH2:20][CH:21]=1

Participants

4

Reactant 1

HCID 57443422HCID 57443422, compound

Product 1

HCID 67453428HCID 67453428, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

797 mg of 4-[allyl-(3-p-tolyl-propyl)-carbamoyl]-pent-4-enoic acid methyl ester (40af) (2.6 mM) prepared by the above Step 6 was added to the catalyst solution containing 180 mg of ruthenium catalyst (0.1 mM) dissolved in 200 ml of 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 (1:1) as an eluant to give 391 mg of 3-[2-oxo-1-(3-p-tolyl-propyl)-2,5-dihydro-1H-pyrrol-3-yl]-propionic acid methyl ester (40ag) (yield: 50%).

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 (1:1) as an eluant

Sources & evidence

ORD record
ord-99201366fb8e4974b092acfb007cab9b
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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