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【结 构 式】 
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【分子编号】50269 【品名】(1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2-carbonyl chloride 【CA登记号】 |
【 分 子 式 】C16H20ClNO 【 分 子 量 】277.79364 【元素组成】C 69.18% H 7.26% Cl 12.76% N 5.04% O 5.76% |
合成路线1
该中间体在本合成路线中的序号：(V)Conjugate addition of 4-tolylmagnesium bromide (II) to anhydroecgonine methyl ester (I) afforded regioselectively the 2-beta-carbomethoxy-3-beta-aryl tropane (III). Hydrolysis of the ester function of (III) in aqueous dioxan gave the corresponding acid (IV). Treatment of (IV) with POCl3 yielded the acid chloride (V), which was condensed with 1,3-propanediol monomesylate (VI), yielding ester (VII). Finally, nucleophilic displacement of the mesylate group of (VII) with tetrabutylammonium fluoride in refluxing THF afforded the title fluoropropyl ester.
| 【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) | 35657 | bromo(4-methylphenyl)magnesium | 4294-57-9 | C7H7BrMg | 详情 | 详情 |
| (III) | 50267 | methyl (1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate | C17H23NO2 | 详情 | 详情 | |
| (IV) | 50268 | (1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid | C16H21NO2 | 详情 | 详情 | |
| (V) | 50269 | (1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2-carbonyl chloride | C16H20ClNO | 详情 | 详情 | |
| (VI) | 50262 | 3-hydroxypropyl methanesulfonate | C4H10O4S | 详情 | 详情 | |
| (VII) | 50270 | 3-[(methylsulfonyl)oxy]propyl (1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate | C20H29NO5S | 详情 | 详情 |