PE2Br
Chemical Name: 8-[3-Bromo-2(E)-propenyl]-3beta-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2beta-carboxylic acid methyl ester
项目整合开发状态: Preclinical
项目研究机构: INSERM (Originator)
合成路线:The reaction of anhydroecgonine methyl ester (I) with 4-methylphenylmagnesium bromide (II) in ethyl ether gives 3beta-(4-methylphenyl)tropane-2beta-carboxylic acid methyl ester (III),which is demethylated by reaction with 2,2,2-trichloroethyl chloroformate (IV) yielding the carbamate (V),followed by reduction with Zn/AcOH to afford the nortropane derivative (VI).The alkylation of (VI) with the tributylstannane (VII),TEA and iodine in ethanol provides the adduct (VIII),which is finally brominated with NBS in THF.
📌 参考资料/链接：
参考文献标题:Synthesis,ligand binding,QSAR,and CoMFA study of 3beta-(p-substitutedphenyl)tropane-2beta-carboxylic acid methyl esters
文献作者:Gao,Y.; Rahman,M.A.; Abraham,P.; Boja,J.W.; Carroll,F.I.; Lewin,A.H.; Kuhar,M.J.; Parham,K.
参考来源:J Med Chem 1991,34(9),2719
📄 详细内容
合成路线:The reaction of anhydroecgonine methyl ester (I) with 4-methylphenylmagnesium bromide (II) in ethyl ether gives 3beta-(4-methylphenyl)tropane-2beta-carboxylic acid methyl ester (III),which is demethylated by reaction with 2,2,2-trichloroethyl chloroformate (IV) yielding the carbamate (V),followed by reduction with Zn/AcOH to afford the nortropane derivative (VI).The alkylation of (VI) with the tributylstannane (VII),TEA and iodine in ethanol provides the adduct (VIII),which is finally brominated with NBS in THF.
参考文献标题:Synthesis of (E)-N-(3-bromoprop-2-enyl)-2 beta-carbomethoxy-3 beta-(4 '-tolyl) nortropane (PE2Br) and radiolabelling of [Br-76]PE2Br: A potential ligand for exploration of the dopamine transporter by PET
文献作者:Helfenbein,J.; et al.
参考来源:J Label Compd Radiopharm 1999,42(6),581
合成路线:By condensation of (-)-anhydroecgonine methyl ester (I) with 4-fluorophenylmagnesium bromide (II) by means of cuprous chloride in refluxing ether.
合成路线:The reaction of anhydroecgonine methyl ester (I) with 4-methylphenylmagnesium bromide (II) in ethyl ether gives 3beta-(4-methylphenyl)tropane-2beta-carboxylic acid methyl ester (III),which is demethylated by reaction with 2,2,2-trichloroethyl chloroformate (IV) yielding the carbamate (V),followed by reduction with Zn/AcOH to afford the nortropane derivative (VI).The alkylation of (VI) with the tributylstannane (VII),TEA and iodine in ethanol provides the adduct (VIII),which is finally brominated with NBS in THF.
参考文献标题:Compounds affecting the central nervous system.4.3beta-Phenyltropane-2-carboxylic esters and analogs
文献作者:Clarke,R.L.; Daum,S.J.; Gambino,A.J.; Aceto,M.D.; Pearl,J.; Levitt,M.; Cumiskey,W.R.; Bogado,E.F.
参考来源:J Med Chem 1973,16(1),1260-67