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Synthesis and Mechanistic Study of Steroidal Oxime Ethers

✍ Scribed by Kamlesh Sharma; Shivani B. Mishra; Ajay K. Mishra

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Reaction of 5__α__‐cholestan‐6‐one oxime (1), its 3__β__‐acetoxy and 3__β__‐chloro analogs, 2 and 3, respectiveley, with ClCH~2~CH~2~NH~2~⋅HCl in presence of MeONa afforded 6‐[(2‐aminoethoxy)imino]‐5__α__‐cholestane (4), 3__β__‐acetoxy‐6‐[(2‐aminoethoxy)imino]‐5__α__‐cholestane (5), and 6‐[(2‐aminoethoxy)imino]‐3__β__‐chloro‐5__α__‐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.

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