Studies on the Steric Inversion of Alkamines. V

On the Steric Inversion of 1, 2-Diphenyl-2-methylaminoethanol-(1)

Abstract

Relationship between substitution reaction and steric rearrangement between erythro and threo compounds of 1, 2-diphenyl-2-methylaminoethanol-(1) was examined and it was found that the situation identical with ephedrine also existed. Treatment of the N-acetyl derivative (VI) of erythro-1, 2-diphenyl-2-methylaminoethanol-(1) (I) with alcoholic hydrochloric acid results in its rearrangement to the O-acetyl derivative (VIII) of the threo series while the threo-1, 2-diphenyl-2-aminoethanol-(1) (II) obtained by the hydrolysis of (VIII) undergoes rearrangement to the N-acetyl (VI) or O-acetyl (VIII) derivative of the erythro-series via threo-chloro (III), erythro-ethylene-imine (IV), and threo-N-acetylchloro (V) derivatives. Hydrolysis of (VI) or (VIII) was found to yield (I).