2-Pyrrolidone → Piperyline

HRID 631939Notes

Reaction equation

HRID 631939 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:29]1[CH2:33][CH2:32][CH2:31][C:30]1=O>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8](/[CH:10]=[CH:11]/[CH:12]=[CH:13]/[C:14]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[O:16])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 682631,1'-CarbonyldiimidazoleHCID 5370536Piperic acid

Product 1

HCID 636537PiperylineYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoic acid (50 mg, 0.23 mmol) was dissolved in 1,1′-carbonyldiimidazole (56 mg, 0.34 mmol) in THF (1.5 mL), followed by stirring for 1 hour. Then, pyrrolidone (0.03 mL, 0.34 mmol) was added thereto, followed by stirring for 6 hours. Upon completion of the reaction, the experiment was completely terminated by addition of distilled water. EtOAc was added to the reaction product to separate an oil layer and a water layer from each other, followed by washing with a saturated solution of NaCl and then drying over anhydrous Na2SO4. The solvent was distilled under reduced pressure. The residue was purified by column chromatography using hexane/ethyl acetate (1/1) to give a target compound (36.1 mg, yield: 58.1%).

Workup

  1. stirringby stirring for 6 hours
  2. customUpon completion of the reaction
  3. customthe experiment was completely terminated by addition of distilled water
  4. additionEtOAc was added to the reaction product
  5. customto separate an oil layer
  6. washby washing with a saturated solution of NaCl
  7. dry with materialdrying over anhydrous Na2SO4
  8. distillationThe solvent was distilled under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bbeb8677cd314d6896a1df4273ca3c52
Source dataset
uspto-grants-2016_04
Patent number
US09321751B2

Reaction notes

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