Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation

Abstract 20-Carboxamidopregnene derivatives, such as 3β-acetoxy-5α-pregn-20-ene-20-carboxamides and 5α-pregn-20-ene-20-carboxamides were synthesized from the widely accessible 3β-acetoxy-pregn-5,16-dien-20-one (PDA) using selective hydrogenation, hydrazine iodoalkene formation, well palladium-catalysed aminocarbonylation. The 20-iodo-20-ene obtained corresponding 20-keto derivatives via their hydrazones, served substrates. 23 new 20-carboxamides various N -nucleophiles ranging simple primary amines to α-amino acid esters. novelty of this methodology lies in application facile, moderate or high-yielding reactions obtain otherwise hardly steroidal pharmaceutical importance. In other words, instead enzymatic synthetic degradation e.g., sterols cholanic acids, functionalization basic skeleton (a ‘building-up’ approach) was used.