Resolution of racemic albuterol via diastereomeric salts formation with di-p-toluoyl-D-tartaric acid.
A convenient method is described for the resolution of racemic Albuterol by selective crystallization of its di-p-toluoyl-D-tartrate salt. The separation resulted in a 38% yield of the (R)-enantiomer. Racemization of the (S)-enantiomer occurs in diluted H2SO4 at 100 degrees C 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.
Ferrayoli
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Ceprocor, Alvarez de Arenales 230, 5000 Córdoba, Argentina.
Palacio
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Bresina
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Palacios
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D000420:Albuterol / Q000737:chemistry / Q000302:isolation & purification*; D012492:Salts; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
D012492:Salts; D013644:Tartrates; C422602:di-p-toluoyltartaric acid; D000420:Albuterol