Acetonitrile → HCID 12621352, compound

HRID 1730167Notes

Reaction equation

HRID 1730167 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:11]([CH3:21])([CH3:20])[N:10]=2)=[CH:5][CH:4]=1.C(#N)C>C(OC(=O)C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:13][C@H:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:11]([CH3:21])([CH3:20])[N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 12621351HCID 12621351, compound

Product 1

HCID 12621352HCID 12621352, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

148 G. of racemic 4-[2-(p-methoxyphenyl)-5,5-dimethyl-1-pyrrolin-4-yl]-pyridine were dissolved in 280 ml. acetonitrile and 450 ml. ethylacetate. 150 G. of (+)-camphersulfonic acid are added and the reaction mixture is heated on a steam bath until all reactants are in solution. The resulting solution is cooled on an ice bath until crystallization begins, then it is allowed to crystallize at room temperature for 2.5 hours. The crystals are filtered and washed with ethyl acetate. The crystals are taken up in water and calcium carbonate is added until a pH 9 is reached and recrystallization occurs. The crystals are filtered, washed with water and taken up in methylene chloride. The organic phase which results is dried over sodium sulfate and evaporated under reduced pressure to obtain crystals of 4-[(4R)-2-(p-methoxyphenyl)-5,5-dimethyl-1-pyrrolin-4-yl]-pyridine: [α]D =-152° (CHCl3, c = 5).

Workup

  1. additionof (+)-camphersulfonic acid are added
  2. temperaturethe reaction mixture is heated on a steam bath until all reactants
  3. temperatureThe resulting solution is cooled on an ice bath until crystallization
  4. customto crystallize at room temperature for 2.5 hours
  5. filtrationThe crystals are filtered
  6. washwashed with ethyl acetate
  7. additioncalcium carbonate is added until a pH 9
  8. customrecrystallization
  9. filtrationThe crystals are filtered
  10. washwashed with water
  11. customThe organic phase which results
  12. dry with materialis dried over sodium sulfate
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bae1dbd8696949db91d6a43136616260
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

Loading…