title: Solvent control of optical resolution of 2-amino-1-phenylethanol using dehydroabietic acid.
abstract: The optical resolution of 2-amino-1-phenylethanol (2-APE) by the solvent switch method was investigated using dehydroabietic acid (DAA), a natural chiral acid obtained as one of the main components of disproportionated rosin. The solvent dependency of optical rotation measurements of 2-APE, DAA and the diastereomeric salts suggested solvent control of optical resolution. Both (R)- and (S)-2-APE were resolved, as the first success for aminoalcohols, only by changing the resolving solvents: (S)-2-APE was obtained in high optical purity by a single crystallization operation with polar solvents (epsilon > 50), whereas the efficiency was lower for (R)-2-APE using less polar solvents (20 < epsilon < 40). The results were compared and discussed with reference to the crystal structures of the diastereomeric salts.
authors.affiliation: Graduate School of Science and Engineering, Saitama University, Shimo-Ohkubo 255, Sakura-ku, Saitama, Saitama 338-8570, Japan.
authors.forename: Kayoko
authors.initials: K
authors.lastname: Taniguchi
authors.forename: Marie
authors.initials: M
authors.lastname: Aruga
authors.forename: Mikio
authors.initials: M
authors.lastname: Yasutake
authors.forename: Takuji
authors.initials: T
authors.lastname: Hirose