Natural nicotinic alkaloids

Nicotine: Nicotine, 1-methyl-2-(3-piridyl)pirrolidine (13.1.27), is an alkaloid that is isolated from the plant Nicotiana (Nicotiana tabacum, Nicotiana rustica, and others) and can be synthesized in various ways [33-36]. In particular, it is proposed to proceed from nicotinic acid ethyl ester, which is condensed with N-methylpyrrolidone, giving 1-methyl-2-nicotinoyl pyrrolidone-2 (13.1.23). Acidic hydrolysis of this compound leads to an opening of the pyrrolidine ring giving the intermediate (13.1.24), which under the reaction conditions is decarboxylated to the /-aminoketone (13.1.25). The carbonyl group is reduced to an alcohol and the resulting product (13.1.26) undergoes dehydration to nicotine (13.1.27).


C2H5ONa i-1 C2H5ONa fY ^-1 H+ ^v.Ach-ch2-ch2-nhch3

CH3 ch3

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