Sodium Acetate → 6-Phenyl-2,3-dihydropyrrolizin-1-one

HRID 880443Notes

Reaction equation

HRID 880443 reaction equation
C([O-])(=O)C.[Na+].C([CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[C:12]1[C:22]([OH:24])=O)(O)=O>C(OC(=O)C)(=O)C>[C:16]1([C:14]2[CH:13]=[C:12]3[N:11]([CH2:10][CH2:9][C:22]3=[O:24])[CH:15]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 669149081-(2-Carboxyethyl)-4-phenylpyrrole-2-carboxylic acid

Product 1

HCID 669147376-Phenyl-2,3-dihydropyrrolizin-1-oneYield 27%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Anhydrous sodium acetate (200 mg, 2.5 mmol) was added to a stirred solution of 1-(2-carboxyethyl)-4-phenyl-pyrrole-2-carboxylic acid (1.0 g, 3.90 mmol) in acetic anhydride (10 mL) and heated at reflux for 16 h. Excess acetic anhydride was evaporated in vacuo and water was added. The mixture was extracted with ethyl acetate and the separated organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the crude product. Purification by column chromatography over neutral alumina using 25% ethyl acetate in petroleum ether as eluent afforded 6-phenyl-2,3-dihydropyrrolizin-1-one (200 mg, 27%) as a brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. customExcess acetic anhydride was evaporated in vacuo and water
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe separated organic layer was washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford the crude product
  11. customPurification by column chromatography over neutral alumina using 25% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-2c45e622837343dd8be9af3773c8304a
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

Loading…