( S)-1-Phenyl-2-( p-tolyl)ethylamine ( S)-1, used for the industrial scale resolution of chrysanthemic acids, was obtained via resolution of the racemate with the hemiphthalate of ( S)-isopropylidene glycerol ( R)-2. The maximum experimental efficiency [69% yield and >99% e.e. of ( S)-1] was achieved by a simple precipitation of ( S)-1·( R)-2 from the solution of the 1:1 diastereomeric salt mixture in 93/7 isopropanol/water at saturation of the more soluble ( R)-1·( R)-2 salt. Such an experimental efficiency was consistent with 0.79 maximum theoretical resolvability, derived from the solubilities of the two diastereomeric salts, and with DSC data, which indicated that the ( S)-1·( R)-2/( R)-1·( R)-2 system is a binary mixture exhibiting an eutectic with composition approximately corresponding to a 0.2 molar ratio of ( S)-1·( R)-2.

Resolution of 1-phenyl-2-( p-tolyl)ethylamine via diastereomeric salt formation / M. Pallavicini, C. Bolchi, B. Moroni, E. Valoti, O. Piccolo. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 14:15(2003), pp. 2247-2251. [10.1016/S0957-4166(03)00440-3]

Resolution of 1-phenyl-2-( p-tolyl)ethylamine via diastereomeric salt formation

M. Pallavicini
Primo
;
C. Bolchi
Secondo
;
B. Moroni;E. Valoti
Penultimo
;
2003

Abstract

( S)-1-Phenyl-2-( p-tolyl)ethylamine ( S)-1, used for the industrial scale resolution of chrysanthemic acids, was obtained via resolution of the racemate with the hemiphthalate of ( S)-isopropylidene glycerol ( R)-2. The maximum experimental efficiency [69% yield and >99% e.e. of ( S)-1] was achieved by a simple precipitation of ( S)-1·( R)-2 from the solution of the 1:1 diastereomeric salt mixture in 93/7 isopropanol/water at saturation of the more soluble ( R)-1·( R)-2 salt. Such an experimental efficiency was consistent with 0.79 maximum theoretical resolvability, derived from the solubilities of the two diastereomeric salts, and with DSC data, which indicated that the ( S)-1·( R)-2/( R)-1·( R)-2 system is a binary mixture exhibiting an eutectic with composition approximately corresponding to a 0.2 molar ratio of ( S)-1·( R)-2.
Settore CHIM/08 - Chimica Farmaceutica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/8517
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