Réaction #10458

Équation de réaction

1,3-dibenzylpyrrolidine-3-carboxylic acid ethyl ester

NaOH

→

title compound

Rendement 76.8%

1,3-Dibenzylpyrrolidine-3-carboxylic acid

Rendement 76.8%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températurethe reaction is heated
2. 2
   Températureto reflux for 24 hours
3. 3
   TempératureThe solution is cooled
4. 4
   Concentrationconcentrated
5. 5
   workup.DISSOLUTIONredissolved in water
6. 6
   Extractionextracted with ether
7. 7
   Autrethe precipitated solid is collected

Mode opératoire

To a solution of 1,3-dibenzylpyrrolidine-3-carboxylic acid ethyl ester (Example A18e, 13.1 g, 41 mmol) in 250 mL of methanol is added 2N NaOH (46 mL, 92 mmol) and the reaction is heated to reflux for 24 hours. The solution is cooled, concentrated, redissolved in water and extracted with ether. The pH of the aqueous layer is adjusted to 7 and the precipitated solid is collected, to give 9.3 g of the title compound, MS EI+: m/z 296 (MH+), mp 209–210° C.

Source