An efficient synthesis of amino-dihydrotestosterone derivative

In this work was synthesized an amino-steroid derivative (4); the route involved preparation of dihydrotestosterone-hemisuccinate (2) by the esterification of dihydrotestosterone (1) using succinic anhydride and pyridine (method A) or using succinic acid and 1,3 dicyclohexylcarbodiimide in presence of p-toluensulfonic acid (method B). After 2 was coupled to 4-hidroxy benzoic acid using 1,3 dicyclohexylcarbodiimide as catalyst to form 3. Finally, 4 was obtained by the reaction between 3 and ethylendiamine hydrochloride in presence of 1-ethyl-3(3-dimethylamino-propyl)carbodiimide.