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【结 构 式】 
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【药物名称】RTI-112 【化学名称】(-)-(1R,2S,3S,5S)-(4-Chloro-3-methylphenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester 【CA登记号】143982-09-6, 150653-92-2 (HCl) 【 分 子 式 】C17H22ClNO2 【 分 子 量 】307.82339 |
【开发单位】Research Triangle Institute (Originator) 【药理作用】Treatment of Cocaine Dependency, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, Dopamine Transporter (DAT) Inhibitors |
合成路线1
Conjugate addition of 4-chloro-3-methylphenylmagnesium iodide (II) to anhydroecgonine methyl ester (I) at -40 C, followed by quenching with trifluoroacetic acid at -78 C afforded a 1:1.6 mixture of 2alpha and 2beta-3-aryltropane-2-carboxylate esters (III). The target 2beta-isomer was then isolated by column chromatography.
| 【1】 Suslu, I.; Altinoz, S.; Med Chem Res 1992, 1, 6, 382-387. |
| 【2】 Carroll, F.I.; Mascarella, S.W.; Kuzemko, M.A.; Gao, Y.; Abraham, P.; Lewin, A.H.; Boja, J.W.; Kuhar, M.J.; Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3beta-(3'-substituted phenyl)-, 3beta-(4'-substituted phenyl)-, and 3beta-(3', 4'-disubstituted phenyl)tropane-2beta-carboxylic acid methyl esters. J Med Chem 1994, 37, 18, 2865. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIIa) | 35050 | methyl (1S,2S,3S,5R)-3-(4-chloro-3-methylphenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | C17H22ClNO2 | 详情 | 详情 | |
| (IIIb) | 35051 | methyl (1S,2R,3S,5R)-3-(4-chloro-3-methylphenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | C17H22ClNO2 | 详情 | 详情 | |
| (I) | 21118 | methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate | C10H15NO2 | 详情 | 详情 | |
| (II) | 35049 | (4-chloro-3-methylphenyl)(iodo)magnesium | C7H6ClIMg | 详情 | 详情 |
Extended Information