Ethyl diazoacetate → 3-Benzyl-2-oxo-3-azabicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester

HRID 484197

Reaktionsgleichung

Reaktionsgleichung von HRID 484197
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]=[CH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N-]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH2:21]([O:20][C:18]([CH:17]1[CH:10]2[CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]2=[O:14])=[O:19])[CH3:22]

Komponenten

4

Edukt 2

HCID 12192Ethyl diazoacetateHCID 111167841-Benzyl-5,6-dihydropyridin-2(1H)-one

Produkt 1

HCID 542844953-Benzyl-2-oxo-3-azabicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 98885Molybdenum carbonyl (Mo(CO)6)Katalysator

Versuchsvorschrift

These compounds can be prepared from 1-benzyl-5,6-dihydro-2(1H)-pyridinone by reaction with ethyl diazoacetate with molybdenum hexacarbonyl catalyst to provide 3-benzyl-2-oxo-3-azabicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester, which can be reduced with lithium aluminum hydride to provide 3-benzyl-7-hydroxymethyl-3-azabicyclo[4.1.0]heptane. Utilization of the methods in Section VIII then yields the desired 7-R7 -substituent.

Quellen und Nachweise

ORD-Eintrag
ord-f9ca0e2e3d454e96925a19fb6a41f1d4
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229396

Verknüpfte Notizen

Wird geladen…