Reaction #64878

ord-d11c6c925c1348ed84d5539cdd66929d

Reaction equation

CC(C)(C)OC(=O)NNC(=O)OC(C)(C)C
hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(C)(COS(C)(=O)=O)COS(C)(=O)=O
2,2-dimethyl-1,3-propanediol dimethanesulfonate
[I-].[K+]
potassium iodide
→
CC1(C)CN(C(=O)OC(C)(C)C)N(C(=O)OC(C)(C)C)C1
desired product
Yield 2.0%
CC1(C)CN(C(=O)OC(C)(C)C)N(C(=O)OC(C)(C)C)C1
4,4-dimethyl-pyrazolidine N,N'-dicarboxylic acid di-tert-buty1 ester
Yield 2.0%

Reactants

CC(C)(C)OC(=O)NNC(=O)OC(C)(C)C
hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(C)(COS(C)(=O)=O)COS(C)(=O)=O
2,2-dimethyl-1,3-propanediol dimethanesulfonate
[I-].[K+]
potassium iodide

Reagents

None

Solvents

CN(C)C=O
N,N-dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction mixture is then concentrated
  2. 2
    workup.ADDITIONdiethyl ether is added
  3. 3
    Washthe organic phase is washed with water
  4. 4
    DryingMter drying over sodium sulfate
  5. 5
    Concentrationthe reaction mixture is concentrated
  6. 6
    Otherpurified by means of column chromatography

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05416065uspto-grants-1995_05