| 吉米沙星关键中间体4-氨甲基吡咯烷-3-酮-O-甲基肟 二盐酸盐的合成方法改进 |
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| 引用本文： | 万志龙,柴 芸,刘明亮,郭慧元.吉米沙星关键中间体4-氨甲基吡咯烷-3-酮-O-甲基肟 二盐酸盐的合成方法改进[J].中国药物化学杂志,2009,19(2):109-111. |
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| 作者姓名： | 万志龙 柴 芸 刘明亮 郭慧元 |
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| 作者单位： | （中国医学科学院 北京协和医学院 医药生物技术研究所，北京100050） |
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| 摘 要： | 目的 合成抗菌药吉米沙星关键中间体4-氨甲基吡咯烷-3-酮-O-甲基肟二盐酸盐。方法 以甘氨酸乙酯盐酸盐为原料，依次经加成、BOC保护氨基、Dieckmann环化、NaBH4还原羰基、LiAlH4还原氰基、BOC保护氨甲基、氧化、肟化、脱BOC保护等9步反应制得目标化合物。结果与结论 合成的目标化合物经1H-NMR和MS谱确证结构，总收率由25.8%提高至39.6%。该合成工艺省去了文献方法中对中间体4和6的柱色谱分离，不经纯化直接用于下步反应，简化了操作步骤。
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| 关 键 词： | 喹诺酮 吉米沙星 中间体 工艺改进 |
| 收稿时间： | 2008-7-16 |
| 修稿时间： | 2009-1-20 |
Improved synthesis of a gemifloxacin intermediate 4-(aminomethyl) pyrrolidin-3-one-O-methyloxime dihydrochloride |
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| WAN Zhi-long,CHAI Yun,LIU Ming-liang,GUO Hui-yuan.Improved synthesis of a gemifloxacin intermediate 4-(aminomethyl) pyrrolidin-3-one-O-methyloxime dihydrochloride[J].Chinese Journal of Medicinal Chemistry,2009,19(2):109-111. |
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| Authors: | WAN Zhi-long CHAI Yun LIU Ming-liang GUO Hui-yuan |
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| Affiliation: | (Institute of Medicinal Biotechnology Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China) |
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| Abstract: | Aim To synthesize a gemifloxacin intermediate, 4-(aminomethyl)pyrrolidin-3-one-O-methyloxime dihydrochloride. Mehods Commercially available glycine ethyl ester hydrochloride was used as starting material to give the target compound via addition, protection with BOC, Dieckmann cyclation, reduction with NaBH4 and LiAlH4, protection, oxidation, oximation and deprotection. Results and conclusion The target compound was prepared in 39.6% overall yield and its structure was identified by 1H-NMR and MS. |
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| Keywords: | quinolone gemifloxacin intermediate process improvement |
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