Optical resolution by preferential crystallization of 4-methylpiperidinium hydrogen (RS)-phenylsuccinate

✍ Scribed by Dr. Tadashi Shiraiwa; Yasunobu Ohki; Yujin Sado; Hideya Miyazaki; Hidemoto Kurokawa

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 401 KB
• Volume: 6
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.530060307

✦ Synopsis

Abstract

Gibbs energy of racemate formation, binary melting point diagram, and ternary solubility diagram suggested that 4‐piperidinium hydrogen (RS)‐phenylsuccinate [(RS)‐4‐MP salt] exists in a conglomerate. Appropriate conditions were explored on the basis of free energy of critical nucleation in a supersaturated solution to resolve efficiently (RS)‐4‐MP salt by preferential crystallization. Successive preferential crystallization of (RS)‐4‐MP salt in ethanol at 20°C gave (R)‐ and (S)‐4‐MP salts of 90–94% optical purities. Optically pure (R)‐ and (S)‐phenylsuccinic acids were obtained by recrystallization of the (R)‐ and (S)‐4‐MP salts, followed by treatment of the salts purified with hydrochloric acid. © 1994 Wiley‐Liss, Inc.