Potassium Iodide → 4,4-dimethyl-pyrazolidine N,N'-dicarboxylic acid di-tert-buty1 ester

HRID 36600Notes

Reaction equation

HRID 36600 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:28][C:29]([CH3:37])([CH3:36])[CH2:30]OS(C)(=O)=O)(=O)=O.[I-].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:30][C:29]([CH3:37])([CH3:36])[CH2:28][N:9]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 85431Di-tert-butyl bicarbamateHCID 299203Neopentyl glycol dimethylsulfate

Product 1

HCID 544895554,4-dimethyl-pyrazolidine N,N'-dicarboxylic acid di-tert-buty1 esterYield 2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

41.8 g of hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester, 74.5 g of potassium carbonate, 52.0 g of 2,2-dimethyl-1,3-propanediol dimethanesulfonate and 2.0 g of potassium iodide are stirred for 48 hours at 120°-130° C. in 360 ml of N,N-dimethylformamide. The reaction mixture is then concentrated; diethyl ether is added and the organic phase is washed with water. Mter drying over sodium sulfate, the reaction mixture is concentrated and purified by means of column chromatography to yield 1.1 g of the desired product, 4,4-dimethyl-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester, in the form of white crystals.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. additiondiethyl ether is added
  3. washthe organic phase is washed with water
  4. dry with materialMter drying over sodium sulfate
  5. concentrationthe reaction mixture is concentrated
  6. custompurified by means of column chromatography

Sources & evidence

ORD record
ord-d11c6c925c1348ed84d5539cdd66929d
Source dataset
uspto-grants-1995_05
Patent number
US05416065

Reaction notes

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