Diethyl Ether → 4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester

HRID 36598Notes

Reaction equation

HRID 36598 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH:13]([OH:15])[CH2:12][N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:9])([CH3:6])([CH3:5])[CH3:4].CI.[CH2:25](OCC)C>CN(C)C=O>[C:19]([O:18][C:16]([N:11]1[CH2:12][CH:13]([O:15][CH3:25])[CH2:14][N:10]1[C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10334299Di-tert-butyl 4-hydroxypyrazolidine-1,2-dicarboxylate

Product 1

HCID 544169224-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At 0°-5° C., 1.2 g of a sodium hydride dispersion (80 %) are added in portions to a solution of 8.6 g of 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in 90 ml of N,N-dimethylformamide. After stiffing for 30 minutes at 0°-5° C., a solution of 2.5 ml of methyl iodide in 10 ml of N,N-dimethylformamide is added dropwise thereto. Stirring is then continued for 3 hours at 0°-5° C. and then 500 ml of diethyl ether are added thereto. The organic phase is washed with water, dried over sodium sulfate and concentrated to yield 8.0 g of the desired product, 4-methoxy-pyrazolidine-N,N'-dicarboxylic acid di-tertbutyl ester, in the form of a yellow oil.

Workup

  1. waitis then continued for 3 hours at 0°-5° C.
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a95fe5a451304b06873d2b8e80483925
Source dataset
uspto-grants-1995_05
Patent number
US05416065

Reaction notes

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