4-[But-3-enyl-(2,4-dimethoxybenzyl)-carbamoyl]-pent-4-enoic acid methyl ester → 3-(1-Benzyl-2-oxo-2,5,6,7-tetrahydro-1H-azepin-3-yl)-propionic acid methyl ester

HRID 2240613Notes

Reaction equation

HRID 2240613 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]([C:8](=[O:25])[N:9]([CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:10][C:11]1[CH:16]=[CH:15][C:14](OC)=[CH:13][C:12]=1OC)=C>C(Cl)Cl.[Ru]>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[C:8](=[O:25])[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:21][CH2:22][CH2:23][CH:24]=1

Participants

4

Reactant 1

HCID 167203324-[But-3-enyl-(2,4-dimethoxybenzyl)-carbamoyl]-pent-4-enoic acid methyl ester

Product 1

HCID 685828973-(1-Benzyl-2-oxo-2,5,6,7-tetrahydro-1H-azepin-3-yl)-propionic acid methyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

150 mg of the compound (c) (0.476 mmol) prepared by the above Step 2 was added to the catalyst solution containing 40 mg of ruthenium (0.047 mmol) dissolved in 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 methanol/chloroform (1:10) solvent mixture as an eluant to give 108 mg of the title compound (d) (yield: 79%).

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 methanol/chloroform (1:10) solvent mixture as an eluant

Sources & evidence

ORD record
ord-9fbda5b7238a4fc4b98cd54ba962a5e4
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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