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【结 构 式】 
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【分子编号】50266 【品名】methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate 【CA登记号】 |
【 分 子 式 】C15H18BrNO2 【 分 子 量 】324.21746 【元素组成】C 55.57% H 5.6% Br 24.65% N 4.32% O 9.87% |
合成路线1
该中间体在本合成路线中的序号：(VI)Conjugate addition of 4-(trimethylsilyl)phenylmagnesium bromide (II) to anhydroecgonine methyl ester (I) afforded regioselectively the 2-beta-carbomethoxy-3-beta-aryl tropane (III). Bromodesilylation of (III) using NaBr and N-chlorosuccinimide gave the bromophenyl derivative (IV). Amine demethylation was accomplished by reaction of (IV) with 1-chloroethyl chloroformate, followed by hydrolysis and decarboxylation of the intermediate carbamate (V) upon treatment with methanol. The resulting secondary amine (VI) was then alkylated with 3-fluoropropyl bromide (VII) to furnish the title fluoropropyl amine.
| 【1】 Gu, X.-H.; et al.; Synthesis and biological evaluation of a series of novel N- or O-fluoroalkyl derivatives of tropane: Potential positron emission tomography (PET) imaging agents for the dopamine transporter. Bioorg Med Chem Lett 2001, 11, 23, 3049. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 21118 | methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate | C10H15NO2 | 详情 | 详情 | |
| (II) | 50257 | bromo[4-(trimethylsilyl)phenyl]magnesium | C9H13BrMgSi | 详情 | 详情 | |
| (III) | 50258 | methyl (1R,2S,3S,5S)-8-methyl-3-[4-(trimethylsilyl)phenyl]-8-azabicyclo[3.2.1]octane-2-carboxylate | C19H29NO2Si | 详情 | 详情 | |
| (IV) | 50264 | methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | C16H20BrNO2 | 详情 | 详情 | |
| (V) | 50265 | 8-(1-chloroethyl) 2-methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate | C18H21BrClNO4 | 详情 | 详情 | |
| (VI) | 50266 | methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate | C15H18BrNO2 | 详情 | 详情 | |
| (VII) | 19812 | 1-bromo-3-fluoropropane | 352-91-0 | C3H6BrF | 详情 | 详情 |