Ethyl diazoacetate → Ethyl-3-benzyloxycarbonyl-3-azabicyclo[4.1.0]heptane-7-carboxylate

HRID 484198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 484198
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N-]>>[CH2:23]([O:22][C:20]([CH:19]1[CH:15]2[CH:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:16]2)=[O:21])[CH3:24]

Komponenten

3

Edukt 2

HCID 12192Ethyl diazoacetateHCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 57155187Ethyl-3-benzyloxycarbonyl-3-azabicyclo[4.1.0]heptane-7-carboxylate

Versuchsvorschrift

Alternatively, 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine can be subjected to reaction with ethyl diazoacetate under rhodium acetate catalysis, to provide ethyl-3-benzyloxycarbonyl-3-azabicyclo[4.1.0]heptane-7-carboxylate. Ester hydrolysis with sodium hydroxide then provides the corresponding carboxylic acid, which can be converted as described in Section VIII to give amino or substituted amino derivatives.

Quellen und Nachweise

ORD-Eintrag
ord-fb3dba690b6d415c96f2b0f7c4406179
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229396

Notizen zur Reaktion

Wird geladen…