Birch reduction of (-)-ephedrine. Formation of a new, versatile intermediate for organic synthesis

G Zvilichovsky, I Gbara-Haj-Yahia

Index: Zvilichovsky, Gury; Gbara-Haj-Yahia, Isra Journal of Organic Chemistry, 2004 , vol. 69, # 15 p. 4966 - 4973

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Citation Number: 13

Abstract

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 ...