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

HRID 275192

Reaction equation

HRID 275192 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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.

Sources & evidence

ORD record
ord-5fa1f061ec9b4aa79a03d4b212a8022f
Source dataset
uspto-grants-1995_02
Patent number
US05391763

Linked notes

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