Liquid Chromatographic Analysis of the Enantiomeric Composition of Norephedrine and Norpseudoephedrine Benzylic Inversion Products

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Abstract
Three of the four stereoisomers of l-phenyl-2-amino-l- propanol (phenylpropanolamine) are available as the single enantiomers. The 1S, 2S-stereoisomer is available only as a component of racemic norpseudoephedrine (S,S- and R,R-1-phenyl-2- amino-1-propanol). The 1S,2S-norpseudoephedrine was prepared from 1RI2S-norephedrine via a benzylic inversion synthetic procedure. This reaction sequence was found to invert the configuration of the benzylic hydroxyl-group in norephedrine and norpseudoephed- rine to yield the corresponding diastereomer. The configuration of the product was determined using reversed-phase liquid chroma- tography following derivatization with 2,3,4,6-tetra-O-acetyl-6-D-glucopyranosyl isothiocyanate (GITC) .