Potassium Iodide → Di-tert-butyl 4-hydroxypyrazolidine-1,2-dicarboxylate

HRID 36597

Reaction equation

HRID 36597 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+].[I-].[K+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:43]([CH:45]1[O:47][CH2:46]1)Br>CC(CC)=O>[C:1]([O:5][C:6]([N:8]1[CH2:46][CH:45]([OH:47])[CH2:43][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

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 85431Di-tert-butyl bicarbamateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 10334299Di-tert-butyl 4-hydroxypyrazolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

46.4 g of hydrazine-N,N'-dicarboxylic acid di-tert-butyl ester, 69.0 g of potassium carbonate, 3.3 g of potassium iodide, 20 ml of tetrabutylammonium fluoride (1 molar solution in tetrahydrofuran) and 21 ml of epibromohydrin are boiled under reflux for 48 hours in 400 ml of ethyl methyl ketone. The resulting suspension is concentrated, and 500 ml of diethyl ether are added thereto; the reaction mixture is then filtered and the tiltrate is concentrated. Purification of the crude product by means of column chromatography yields 27.1 g of the desired 4-hydroxy-pyrazolidine-N,N'-dicarboxylic acid di-tert-butyl ester in the form of white crystals; m.p. 100°-102° C.

Workup

  1. concentrationThe resulting suspension is concentrated
  2. addition500 ml of diethyl ether are added
  3. filtrationthe reaction mixture is then filtered
  4. concentrationthe tiltrate is concentrated
  5. customPurification of the crude product by means of column chromatography

Sources & evidence

ORD record
ord-da71adb801284935aabd431835879a32
Source dataset
uspto-grants-1995_05
Patent number
US05416065

Linked notes

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