(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. © 2003 Elsevier Ltd. All rights reserved.
Pallavicini, M., Bolchi, C., Moroni, B., Valoti, E., & Piccolo, O. (2003). Resolution of 1-phenyl-2-(p-tolyl)ethylamine via diastereomeric salt formation. Tetrahedron Asymmetry, 14(15), 2247–2251. https://doi.org/10.1016/S0957-4166(03)00440-3