Metanicotine, TC-240312, TC-2403, RJR-2403
位变异烟碱Chemical Name: N-Methyl-4-(3-pyridyl)-3(E)-buten-1-amine
CAS No. 538-79-4, 515836-09-6 (oxalate salt (1:1)), 5960-10-1 (tartrate)
项目整合开发状态: Phase II
项目研究机构: R.J. Reynolds Tobacco (Originator), Targacept (Originator), Falk Pharma (Codevelopment)
合成路线:Nicotine (I) is converted to the N-oxide (II) by oxidation with m-chloroperbenzoic acid.Treatment of N-oxide (II) with ferric nitrate gives rise to a number of different products,among them,the hydroxylamine (III) arises by a Cope elimination process.The target metanicotine is formed by reduction of hydroxylamine (III) as a minor reaction product
📌 参考资料/链接：
参考文献标题:The formation of 1-methyl-3-nicotinoylpyrrolidine from nicotine 1'-oxide
文献作者:Joyce,N.J.; Leete,E.
参考来源:Heterocycles 1989,29(7),1335
📄 详细内容
合成路线:Treatment of nicotine (I) with ethyl chloroformate produces the open-chain chloro carbamate (II) which,upon distillation,undergoes elimination to the N-pyridylbutenyl carbamate (III).Acidic hydrolysis of the carbamate group of (III) then provides the target metanicotine
参考文献标题:Transformations involving the pyrrolidine ring of nicotine
文献作者:Acheson,R.M.; et al.
参考来源:J Chem Soc - Perkins Trans I 1980,(2),579
产品链接: CAS No. 538-79-4››