Hydrochloric Acid → Benzyl 4-methylidenepyrazolidine-1-carboxylate

HRID 413033

Reaction equation

HRID 413033 reaction equation
C(OC([N:8]1[CH2:12][C:11](=[CH2:13])[CH2:10][N:9]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=O)(C)(C)C.S(Cl)(Cl)=O.Cl>CO>[CH2:17]([O:16][C:14]([N:9]1[CH2:10][C:11](=[CH2:13])[CH2:12][NH:8]1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 12970152Benzyl tert-butyl 4-methylidenepyrazolidine-1,2-dicarboxylate

Product 1

HCID 12970153Benzyl 4-methylidenepyrazolidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude 4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 1, (30 g) in methanol (300 mL) is added thionyl chloride dropwise at 0° C. The reaction is warmed to room temperature and stirred an additional 18 hours. Concentration of the reaction in vacuo affords a yellow oil which crystallizes upon standing to provide 23 g (97% yield) of the desired product as the HCl salt.

Workup

  1. customConcentration of the reaction in vacuo
  2. customaffords a yellow oil which
  3. customcrystallizes

Sources & evidence

ORD record
ord-af422b1a592b4583b747bf5daf50f0f5
Source dataset
uspto-grants-2003_05
Patent number
US06566357B1

Linked notes

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