4-(2-Pyridyl)Benzoic Acid → Methyl (2S,4EZ)-4-(methoxyimino)-1-[4-(2-pyridinyl)benzoyl]-2-pyrrolidinecarboxylate

HRID 457927Notes

Reaction equation

HRID 457927 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7]([C:9]([O:11]C(C)(C)C)=O)[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:34]=[CH:33][C:29](C(O)=O)=[CH:28][CH:27]=1>>[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7]([C:9](=[O:11])[C:29]2[CH:28]=[CH:27][C:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)=[CH:34][CH:33]=2)[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1

Participants

3

Reactant 2

HCID 8216924-(2-Pyridyl)Benzoic AcidHCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 131726287Methyl (2S,4EZ)-4-(methoxyimino)-1-[4-(2-pyridinyl)benzoyl]-2-pyrrolidinecarboxylateYield 45%

Procedure

Following the general method as outlined in Example 4 (Method B), starting from 1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate and 4-(2-pyridinyl)benzoic acid, the title compound was obtained, after flash-chromatography (eluent cyclohexane/ethyl acetate 8:2), as a mixture of two isomers in 45% yield (95% purity by HPLC).

Sources & evidence

ORD record
ord-f71ea80d3ee649ec922ac94b30d066f0
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

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