Synthesis and characterization of 1-(1-(4- methoxyphenyl)vinyl)stanninane as a serotonin/noradrenaline reuptake inhibitor precursor compound

The aim of this study was to synthesize and characterize a more effective tin bioisoster of a biologically active carbon-based chemical compound. At the center of the research is the synthesis and characterization of 1-(1-(4-methoxyphenyl)vinyl) stanninane, a precursor of stanna-venlafaxine, the tin analog of the serotonin/noradrenaline reuptake inhibitor venlafaxine. It is thought that this compound and its various derivatives will have potential for use in biotechnological applications. When synthesizing the tin precursor compound, the methods used in the synthesis of carbon, silicon or germanium derivatives of similar compounds known in the literature were utilized. However, since the tin element had different behaviors than silicon and germanium in forming the organometallic compound, it was necessary to adapt and modify the synthesis routes to tin chemistry. According to this; Stanna-cyclohexane formed by the reaction of SnCl4 with the previously prepared Grignard compound was derivatized with a lithium amide compound. 1,1-dimethoxy-1-stannacyclohexane, formed by the reaction of the amide derivative of stanna-cyclohexane with methanol, reacts with the previously prepared 1-methoxyacetophenone-2,4,6-triisopropylbenzene sulfonylhydrazone (Chamberlin 1978) compound to form 1-methoxy-1-[1-(4-methoxyphenyl)vinyl]-1-stannacyclohexane (Shapiro reaction). The final product was obtained by a reduction reaction with lithium aluminum hydride. All products were characterized by 1H-,13C-NMR and IR spectroscopy.