ISOPROPYLIDENE GLYCEROL HYDROGEN PHTHALATE - A NEW RESOLVING AGENT - APPLICATION TO THE RESOLUTION OF 1-ARYLETHYLAMINES

Hydrogen phthalates of (R)- and (S)-isopropylidene glycerol, obtainabl e from racemic isopropylidene glycerol by reaction with phthalic anhyd ride and successive resolution with (S)- and (R)-1-phenylethylamine or , alternatively, from (R)-and (S)-isopropylidene glycerol, were regard ed as potential new resolving agents. A range of important 1-arylethyl amines was selected to test their resolving capability In particular, trial resolutions were carried out using equivalent amounts of racemic amine and hydrogen phthalate of (R)isopropylidene glycerol. The salts of the S isomers selectively crystallized from methanol or 2-propanol allowing to recover the (S)-1-arylethylamines in high chemical and op tical yields. Copyright (C) 1996 Elsevier Science Ltd