Synthesis and Mechanistic Study of Steroidal Oxime Ethers

Reaction of 5a-cholestan-6-one oxime (1), its 3 beta-acetoxy and 3 beta-chloro analogs, 2 and 3, respectiveley, with ClCH2CH2NH2 center dot HCl in presence of MeONa afforded 6-[(2-aminoethoxy)imino]-5a-cholestane (4), 3 beta-acetoxy-6-[(2-aminoethoxy)imino]-5a-cholestane (5), and 6-[(2-aminoethoxy)imino]-3 beta-chloro-5a-cholestane (6), respectively. The structures of newly synthesized compounds have been established on the basis of physical, analytical, and spectral data. Theoretical calculations were assessed by using DFT at B3LYP/6-31G* level to describe the mechanism of the reaction. The stability and feasibility of all the generated structures studied in this report were supported by their respective fundamental frequencies and energy minima.