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