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 (ε > 50), whereas the efficiency was lower for (R)-2-APE using less polar solvents (20 < ε < 40). The results were compared and discussed with reference to the crystal structures of the diastereomeric salts.