Synthesis and design of a progesterone-alkyne derivative

In this work a progesterone-alkyne derivative was synthesized. The first stage involves preparation of a progesterone-ethylenediamine derivative (2) by the reaction of progesterone with ethylenediamine using Mannich reaction. The second stage involves the formation of ethylenediamine-progesterone oxime (4) by the reaction of 2 with hydroxylamine hydrochloride (Method A). Additionally, 4 was also synthesized by the reaction of pregn-4-ene-3E,20E-dioxime (3) with ethylenediamine using Mannich reaction (method B). Finally, the route for synthesis of progesterone-alkyne derivative (5) was followed using a three-component system (compound 4, benzaldehyde and 1-hexyne) in the presence of anhydrous cupric chloride.