Resolution of Racemic Albuterol Via Diasteromeric Salts Formation With Di-p-toluoyl-D-Tartaric Acid

FERRAYOLI CARLOS; PALACIO, MARCELA; BRESINA M FERNANDA; PALACIOS SARA

Enantiomer: A Journal of Sterochemistry

Año: 2000 vol. 5 p. 289 - 291

1024-2430

A convenient method is described for the resolution of racemic albuterol by selective crystallization of its di-p-toluoyl-D-tartaric salt. The separation resulted in a 38% yield of the (R)-enantiomer. Racemization of the (S)-enantiomer occurs in diluted H2SO4 at 100ºC in 80% yield. This racemic mixture was recycled to the diastereomer salt, in order to improve the overall yield. The (R)-Albuterol tartrate salt was decomposed in a sulfuric acid solution, and the (R)-Albuterol was isolated as its sulfate salt with 67% overall yield with 99.5% optical purity.