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

HRID 484198Notes

Reaction equation

HRID 484198 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Sources & evidence

ORD record
ord-fb3dba690b6d415c96f2b0f7c4406179
Source dataset
uspto-grants-1993_07
Patent number
US05229396

Reaction notes

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