Acetonitrile → HCID 12621352, compound

Participants

Reaction Steps

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).

Provenance & Evidence