Synthesis and Hydrolysis of (N-L-Ephedrinyl)cyano(p-methoxyphenyl)methane

摘要

Ephedrine alkaloids react with glcyolic acid nitrile to give aminoacetonitriles [1] whose acid hydrolysis yields 2-morpholones [2]. We have prepared #alpha#-amino nitrile I from L-ephedrine and p-methoxybenzaldehyde. Acid hydrolysis of amino nitrile I yields as the final product cyclic compound II. This unusual reaction pathway probably involves intramolecular nucelophilic attack of the hydroxy group at the carbonyl carbon atom of the less stable intermediate #alpha#-amino amide.