3-Oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester → tert-Butyl 3-oxo-2,3,5,6,8,9-hexahydro-7H-pyridazino[3,4-d]azepine-7-carboxylate

HRID 239163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 239163
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2=[N:15][NH:16][C:17](=[O:19])[CH2:18][CH:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2=[N:15][NH:16][C:17](=[O:19])[CH:18]=[C:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 1

HCID 866865123-Oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

Produkt 1

HCID 86686513tert-Butyl 3-oxo-2,3,5,6,8,9-hexahydro-7H-pyridazino[3,4-d]azepine-7-carboxylateAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

7 g 3-oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester was dissolved in 70 mL toluene and 6.7 g manganese dioxide was added to the reaction mixture. It was heated at reflux for 48 h. After completion of the reaction, the reaction mixture was diluted with chloroform and filtered through celite. The filtrate was concentrated and purified by column chromatography to afford 5.5 g of the desired product. (M+H)+=266

Aufarbeitung

  1. temperatureIt was heated
  2. temperatureat reflux for 48 h
  3. customAfter completion of the reaction
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b4b091f182684dce8868f11e52bdc5ef
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642774B2

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