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 2240613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240613
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23950RutheniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9fbda5b7238a4fc4b98cd54ba962a5e4
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723376B2

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