AbstractHomoveratrylamine was condensed with 1‐cyanocyclopentene to afford the corresponding 2‐cyano‐N‐(3,4‐dimethoxyphenethyl)cyclopentylamine (III), which was ethoxycarbonylated with ethyl chlorocarbonate to give thetrans‐urethan (IVt) (major product) and thecis‐urethan (IVc) which could be separated through a silica gel column. Thecis‐urethan was converted to thetrans‐urethan by the action of a catalytic amount of sodium ethoxide. Based upon general considerations of nucleophilic addition such as the Michael type reaction, the physical data obtained, and the difference in ease of cyclization of the 2‐aminomethyl‐N‐ethoxycarbonyl‐.N‐homoveratrylcyclopentylamines (Vt and Vc) to the corresponding cyclic ureas (Vlt and VIc), it was concluded that the major product was thetransand the minor thecisisomer.The cyclized compounds, Vlt and VIc, were subsequently submitted to the Bischler‐Napieralski reaction furnishing the corresponding isoquinoline derivatives respectively. Thus the authors established a skeletal synthesis of the title compound, a 8,11‐diazasteroid, and its stereochemical configuration at the C