4-(3-Methyl-2-pyridinyl)benzoic acid → Methyl (2S,4EZ)-4-(methoxyimino)-1-[4-(3-methyl-2-pyridinyl)benzoyl]-2-pyrrolidinecarboxylate

HRID 457928Notes

Reaction equation

HRID 457928 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.[CH3:20][C:21]1[C:22]([C:27]2[CH:35]=[CH:34][C:30](C(O)=O)=[CH:29][CH:28]=2)=[N:23][CH:24]=[CH:25][CH:26]=1>>[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7]([C:9](=[O:11])[C:30]2[CH:34]=[CH:35][C:27]([C:22]3[C:21]([CH3:20])=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:28][CH:29]=2)[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1

Participants

3

Reactant 2

HCID 219373114-(3-Methyl-2-pyridinyl)benzoic acidHCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 131726288Methyl (2S,4EZ)-4-(methoxyimino)-1-[4-(3-methyl-2-pyridinyl)benzoyl]-2-pyrrolidinecarboxylateYield 50%

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-(3-methyl-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 50% yield (100% purity by HPLC).

Sources & evidence

ORD record
ord-0d083749aaf94148b6d39fbf3be71131
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

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