Reaction #7752

Reaction equation

4-(2,2-Dimethylpropionyloxy)pyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Thionyl chloride

HCl

→

desired product

Yield 98.0%

4-(2,2-dimethylpropionyloxy)pyrazolidine-1-carboxylic acid 1-benzyl ester

Yield 98.0%

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   ConcentrationThe reaction solution is concentrated in vacuo
3. 3
   Otherto give

Procedure

4-(2,2-Dimethylpropionyloxy)pyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 29, (1.76 g, 4.33 mmol) is dissolved in methanol (40 mL) and the solution cooled to 0° C. Thionyl chloride (3.16 mL, 43.3 mmol) is added dropwise and the reaction allowed to warm to room temperature and continue stirring 12 hours. The reaction solution is concentrated in vacuo to give afford 1.45 g (98% yield) of the desired product as the HCl salt as an off-white solid.

Source