Design and synthesis of estrogen derivative

In this study, an estrogen derivative was synthesized. The first stage involves the synthesis of 17-(2-amino-ethylimino)-13-methyl-7,8,9,11,12,13,14, 15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-ol (3) by the reaction of estrone with ethylenediamine using boric acid as catalyst. The second stage was achieved by reaction of compound 3 with chloroacetyl chloride in presence of triethylamine to form N-{2-[(3-chloro-2-oxo-cyclobutyl)-(3-hydroxy-13-methyl-7, 8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren- 17-yl)-amino]ethylcarbamic chloride (5). The third stage was achieved by reaction of compound 5 with thiourea to form 2-[(2-aminoethyl)-(3-hydroxy-13- methyl-7,8,9,11,12,13,14,15,16-17-decahydro-6H-cyclopenta[a]phenanthren-17-yl) amino]-4-chloro-cyclobutanone (7) in methanol. The structures of compounds obtained were confirmed by spectroscopically.