Chlorodifluoromethane → 4-difluoromethoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester

HRID 36599

Reaction equation

HRID 36599 reaction equation
[OH-].[K+].[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].Cl[CH:24]([F:26])[F:25]>O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:19]([O:18][C:16]([N:11]1[CH2:12][CH:13]([O:15][CH:24]([F:26])[F: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 3

HCID 6372ChlorodifluoromethaneHCID 14797Potassium HydroxideHCID 10334299Di-tert-butyl 4-hydroxypyrazolidine-1,2-dicarboxylate

Product 1

HCID 537794724-difluoromethoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl esterYield 33.3%

Reagents, catalysts & solvents 2

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.2 g of tetrabutylammonium fluoride and 5.6 g of potassium hydroxide powder are added to a solution of 6.9 g of 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in 60 ml of tetrahydrofuran. At a maximum of 45° C., 8.0 g of chlorodifluoromethane are introduced. The reaction solution is then filtered, concentrated and purified by means of column chromatography to yield 2.7 g of the desired product, 4-difluoromethoxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester, in the form of a yellow oil.

Workup

  1. filtrationThe reaction solution is then filtered
  2. concentrationconcentrated
  3. custompurified by means of column chromatography

Sources & evidence

ORD record
ord-ab3109325d83479eba6f59e9863eaba5
Source dataset
uspto-grants-1995_05
Patent number
US05416065

Linked notes

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