Hydrazine hydrate (1:1) → tert-butyl (2S,4EZ)-2-(hydrazinocarbonyl)-4-(methoxyimino)-1-pyrrolidinecarboxylate

HRID 1242548Notes

Reaction equation

HRID 1242548 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:6]([C:16]([O:18]C)=O)[CH2:5]1.[NH2:20][NH2:21].O>CO>[NH:20]([C:16]([C@@H:6]1[CH2:5][C:4](=[N:3][O:2][CH3:1])[CH2:8][N:7]1[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[O:18])[NH2:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 58714558tert-butyl (2S,4EZ)-2-(hydrazinocarbonyl)-4-(methoxyimino)-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate (1.95 mmoles; 530 mg) was dissolved in 4 mL of MeOH and a solution of 4 mL of MeOH and 1.5 mL (d=1.03; 30.86 mmoles) of 80% hydrazine.hydrate was added (final c(NH2NH2)=13%). The reaction mixture was agitated for 2 days. Solvents were evaporated in vacuo and the residue re-dissolved in MeOH and evaporated (3×). The desired compound, tert-butyl (2S,4EZ)-2-(hydrazinocarbonyl)-4-(methoxyimino)-1-pyrrolidinecarboxylate, was isolated as a yellow oil (500 mg; 94%).

Workup

  1. customSolvents were evaporated in vacuo
  2. dissolutionthe residue re-dissolved in MeOH
  3. customevaporated (3×)

Sources & evidence

ORD record
ord-83a6daa381b146319432e3f44e9e2555
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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