The reduction of (-)-ephedrine by lithium in liquid ammonia resulted in the formation of S-1- (1, 4-cyclohexadien-1-yl)-N-methyl-2-propanamine. In addition to the reduction of the aromatic ring, the hydroxy group was reduced as well. The resulting 1, 4-cyclohexadienyl group is a potentially versatile intermediate for further synthetic transformations. The ozonolysis of this group was investigated, producing derivatives of β-keto-δ-methylamino ...
