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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。
OBJECTIVE To synthesize 4-aminomethylpyrrolidin-3-one-O-methyloxime dihydrochloride, the key intermediate of antimicrobial gemifloxacin. Methods Glycine ethyl ester hydrochloride was used as raw material, followed by addition, Boc protection, Dieckmann cyclization, NaBH4 reduction, LiAlH4 reduction, Boc protection of aminomethyl, oxidation, oximation and deprotection in 9 steps The target compound was obtained by reaction. Results and Conclusion The target compounds were confirmed by 1H-NMR and MS spectra. The overall yield increased from 25.8% to 39.6%. This synthetic procedure eliminates the need for column chromatography of intermediates 4 and 6 in the literature method and is used directly in the next step without purification, simplifying the procedure.