立体选择性合成内型N-Boc-N-去甲托品醇 |
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引用本文: | 房元英,王琦,李志峰,金一,许军,杨尊华.立体选择性合成内型N-Boc-N-去甲托品醇[J].合成化学,2015,23(10):957-959. |
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作者姓名: | 房元英 王琦 李志峰 金一 许军 杨尊华 |
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作者单位: | 1. 江西中医药大学 中药固体制剂制造技术国家工程研究中心,江西 南昌 330006; 2. 江西中医药大学 药学院,江西 南昌 330004 |
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基金项目: | 国家自然科学基金资助项目(81460526) |
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摘 要: | 以托品酮为起始原料,与氯甲酸氯乙酯经脱甲基化反应制得脱甲基托品酮(1); 1与Boc酸酐反应制得N-Boc-N-去甲托品酮(2);以三仲丁基硼氢化锂为还原剂,2经还原反应立体选择性合成了内型N-Boc-N-去甲托品醇(内型/外型=6.5/1),总收率60%,其结构经1H NMR和ESI-MS确证。
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关 键 词: | 托品酮 三仲丁基硼氢化锂 内型-N-Boc-N-去甲托品醇 立体选择性合成 |
收稿时间: | 2015-06-25 |
Stereoselective Synthesis of Endo-N-Boc Nortropine |
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Institution: | 1. National Engineering Research Center for Manufacturing Technology of TCM Solid Preparation, Jiangxi University of Traditional Chinese Medicine, Nanchang 330006, China; 2. College of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China |
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Abstract: | Demethylated tropinone(1) was synthesized by reaction of tropinone with 1-chloroethyl chloroformate. N-Boc nortropinone(2) was prepared by reaction of 1 with Boc anhydride. 2 was reduced by lithium tri-sec-butylborohydride to achieve endo-N-Boc nortropine stereoselectively(endo/exo=6.5/1) with an overall yield of 60%. The structure was confirmed by 1H NMR and ESI-MS. |
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Keywords: | tropinone L-selectride endo-N-Boc nortropine stereoselective synthesis |
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