Sodium Hydroxide → 1,3-Dibenzylpyrrolidine-3-carboxylic acid

HRID 10362Notes

Reaction equation

HRID 10362 reaction equation
C([O:3][C:4]([C:6]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[CH2:11]([N:8]1[CH2:9][CH2:10][C:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:4]([OH:5])=[O:3])[CH2:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69071489HCID 69071489, compound

Product 1

HCID 219793511,3-Dibenzylpyrrolidine-3-carboxylic acidYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe solution is cooled
  4. concentrationconcentrated
  5. dissolutionredissolved in water
  6. extractionextracted with ether
  7. customthe precipitated solid is collected

Sources & evidence

ORD record
ord-a9a5e5f0de004235805830ca3e08b53b
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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