RTI-362
Chemical Name: 3alpha-(4-Methylphenyl)nortropane-2beta-carboxylic acid methyl ester; 3endo-(4-Methylphenyl)-8-azabicyclo[3.2.1]octane-2exo-carboxylic acid methyl ester
项目整合开发状态: Biological Testing
项目研究机构: National Institute on Drug Abuse (Originator), Research Triangle Institute (Originator)
合成路线:Treatment of azabicyclo[3.2.1]octene derivative (I) with lithiated compound (II) in THF followed by quenching with trifluoroacetic acid yields tropane (III),whose oxadiazole group is converted into a methyl ester by treatment with nickel boride (Ni2B) and HCl in refluxing methanol to provide the 2-beta,3-alpha stereoisomer (IV).Finally,the desired nortropane compound is obtained by refluxing tropane (IV) with alpha-chloroethyl chloroformate (ACE-Cl) in dichloromethane followed by solvolysis with methanol.
📌 参考资料/链接：
参考文献标题:3alpha-(4'-Substituted phenyl)tropane-2beta-carboxylic acid methyl esters: Novel ligands with high affinity and selectivity at the dopamine transporter
文献作者:Holmquist,C.R.; Keverline-Frantz,K.I.; Abraham,P.; Boja,J.W.; Kuhar,M.J.; Carroll,F.I.
参考来源:J Med Chem 1996,39(21),4139
📄 详细内容
合成路线:Treatment of azabicyclo[3.2.1]octene derivative (I) with lithiated compound (II) in THF followed by quenching with trifluoroacetic acid yields tropane (III),whose oxadiazole group is converted into a methyl ester by treatment with nickel boride (Ni2B) and HCl in refluxing methanol to provide the 2-beta,3-alpha stereoisomer (IV).Finally,the desired nortropane compound is obtained by refluxing tropane (IV) with alpha-chloroethyl chloroformate (ACE-Cl) in dichloromethane followed by solvolysis with methanol.
参考文献标题:3alpha-(4-Substituted phenyl) mortropane-2beta-carboxylic acid methyl esters show selective binding at the norepinephrine transporter
文献作者:Blough,B.E.; Holmquist,C.R.; Abraham,P.; Kuhar,M.J.; Carroll,F.I.
参考来源:Bioorg Med Chem Lett 2000,10(21),2445