Trifluoroacetic acid → methyl-(2S,4EZ)-4-(methoxyimino)2-pyrrolidinecarboxylate

HRID 457920Notes

Reaction equation

HRID 457920 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7](C(OC(C)(C)C)=O)[C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]1[CH2:8][NH:7][C@H:6]([C:16]([O:18][CH3:19])=[O:17])[CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 123256627methyl-(2S,4EZ)-4-(methoxyimino)2-pyrrolidinecarboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution was made containing e.g. 1-tert-Butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate (0.892 g, 3.28 mmol), in anhydrous DCM (28 ml). TFA (20%, 7 mL) was added dropwise. The mixture was stirred at r.t. for 20 min. Solvents were evaporated and the desired product, e.g. methyl (2S,4EZ)-4-(methoxyimino)-2-pyrrolidinecarboxylate (0.564 g, quant.) was isolated as a yellow oil and used without further purification.

Workup

  1. customSolvents were evaporated

Sources & evidence

ORD record
ord-f00c25c207de45cda9ba10c3db19e693
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

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