1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate → methyl-(2S,4EZ)-4-(methoxyimino)2-pyrrolidinecarboxylate

HRID 457921Notes

Reaction equation

HRID 457921 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(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

3

Reactant 1

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

Product 1

HCID 123256627methyl-(2S,4EZ)-4-(methoxyimino)2-pyrrolidinecarboxylateYield 100.3%

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 (60 mg, 0.22 mmol), in anhydrous DCM (6 ml). At 0° C., HCl gas was bubbled slowly through the reaction and the deprotection was followed by TLC. After approximately 30 minutes, the DCM was evaporated. The product was concentrated in vacuo from DCM (2–3 times) to remove the HCl. The desired product, e.g. methyl (2S,4EZ)-4-(methoxyimino)-2-pyrrolidinecarboxylate (38 mg, quant.) was isolated as a yellow solid and used without further purification.

Workup

  1. customAt 0° C., HCl gas was bubbled slowly through the reaction
  2. customthe DCM was evaporated
  3. concentrationThe product was concentrated in vacuo from DCM (2–3 times)
  4. customto remove the HCl

Sources & evidence

ORD record
ord-ad4b212d98674911918fa7ca10fd089e
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

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