HCID 57443411, compound → HCID 57443412, compound

HRID 2240571Notes

Reaction equation

HRID 2240571 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]([C:8](=[O:24])[N:9]([CH2:21][CH:22]=C)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[O:19][CH3:20])=C>C(Cl)Cl.[Ru]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[C:8](=[O:24])[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])[CH2:21][CH:22]=1

Participants

4

Reactant 1

HCID 57443411HCID 57443411, compound

Product 1

HCID 57443412HCID 57443412, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

324 mg of the compound (1c) (0.933 mM) prepared by the above Step 2 was added to the catalyst solution containing 74 mg of ruthenium (0.09 mM) dissolved in 93 ml of CH2Cl2. 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 268 mg of 3-[1-(2,4-dimethoxybenzyl)-2-oxo-2,5-dihydro-1H-pyrole-3-yl]-propionic acid methyl ester (1d) (yield: 90%).

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-d03c9db5f0974eaeac1c23ec1218d7ee
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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