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

HRID 373687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373687
[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-c643b0d121824191a09dcc1b7f674977
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164402

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