Isopropylidene glycerol hydrogen phthalate: A new resolving agent. Application to the resolution of 1-arylethylamines

Hydrogen phthalates of (R)- and (S)-isopropylidene glycerol, obtainable from racemic isopropylidene glycerol by reaction with phthalic anhydride and successive resolution with (S)- and (R)-1-phenylethylamine or, alternatively, from (R)-and (S)-isopropylidene glycerol, were regarded as potential new resolving agents. A range of important 1-arylethylamines 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 optical yields. Copyright (C) 1996 Elsevier Science Ltd