Abstract
Nagai and Kanao converted dl-N-benzoyl-norephedrine through the oxazoline into the diastereoisomeric dl-N-benzoylnorisoephedrine. This oxazoline inversion can be utilized to convert dl-erythro-1-phenyl-2-acetamido-1, 3-propanediol (V) into the dl-threo compound (IX). The erythro compound forms 2-methyl-4-hydroxymethyl-5-phenyl-Δ2-trans-oxazoline (VII) by treatment with thionyl chloride and sodium carbonate. On treatment with diluted mineral acids, the oxazoline (VII) gives O-acetyl compound (VIII) which can be rearranged to dl-threo-1-phenyl-2-acetamido-1, 3-propanediol (IX) with ammonia.
