合成路线:Milameline can be obtained by three related ways:1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF.2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III),which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV).Finally,this compound is hydrogenated with NaBH4 in methanol/water.3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI),which is then alkylated with methyl iodide in DMF.
参考文献标题:O-Substd.tetrahydropyridine oxime cholinergic agents
文献作者:Bergmeier,S.C.; Downs,D.A.; Moos,W.H.; Moreland,D.W.; Tecle,H.(Pfizer Inc.)
参考来源:AU 8781102; EP 0271798; JP 1988215664; US 4710508
合成路线:Milameline can be obtained by three related ways:1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF.2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III),which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV).Finally,this compound is hydrogenated with NaBH4 in methanol/water.3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI),which is then alkylated with methyl iodide in DMF.
参考文献标题:Milameline Hydrochloride
文献作者:Graul,A.; Castar,J.
参考来源:Drugs Fut 1996,21(11),1124
合成路线:Milameline can be obtained by three related ways:1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF.2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III),which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV).Finally,this compound is hydrogenated with NaBH4 in methanol/water.3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI),which is then alkylated with methyl iodide in DMF.
参考文献标题:1-Alkyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyl-oximes: A new class of potent orally active muscarinic agonists related to arecoline
文献作者:Toja,E.; Bonetti,C.; Butti,A.; Hunt,P.; Fortin,M.; Barzaghi,F.; Formento,M.L.; Maggioni,A.; Nencioni,A.; Galliani,G.
参考来源:Eur J Med Chem 1991,26(9),853-68
产品链接: CAS No. 139886-04-7›› 产品链接: CAS No.139886-32-1››