• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
LAI Zengwei, XU Li, SONG Zhuang, LEI Xiantao, XU Qinglong, SUN Hongbin. Asymmetric synthesis of an amine-azaspiro as the key intermediate of sitafloxacin[J]. Journal of China Pharmaceutical University, 2014, 45(4): 400-404. DOI: 10.11665/j.issn.1000-5048.20140403
Citation: LAI Zengwei, XU Li, SONG Zhuang, LEI Xiantao, XU Qinglong, SUN Hongbin. Asymmetric synthesis of an amine-azaspiro as the key intermediate of sitafloxacin[J]. Journal of China Pharmaceutical University, 2014, 45(4): 400-404. DOI: 10.11665/j.issn.1000-5048.20140403

Asymmetric synthesis of an amine-azaspiro as the key intermediate of sitafloxacin

More Information
  • As an important intermediate of quinolone antibacterial agents such as sitafloxacin and olamufloxacin, 7-(S)-tert-butoxycarbonylamino-5-azaspiro[2. 4]heptane has received much attention. Previous syntheses suffered from low yielding and poor stereoselectivity. In this study, an asymmetric synthetic approach was developed to optically pure amine-azaspiro compound with convenient manipulation, excellent yields and high stereoselectivity.
  • [1]
    Kimura K,Atarashi S,Kawakami K,et al.(Fluorocyclopropyl)quinolones.2 Synthesis and stereochemical structure-activity relationships of chiral 7-(7-amino-5-azaspiro[2.4] heptan-5-yl)-1-(2-fluorocyclopropyl)quinolone antibacterial agents[J].J Med Chem,1994,37(20):3 344-3 352.
    [2]
    Liu M,Liu XR.The antimicrobial drug sitafloxacin hydrate[J].Shanghai Pharm(上海医药),2010,31(3):122-124.
    [3]
    Chen GB,Yue LJ.Research progress on the synthesis of sitafloxacin[J].Chin J Syn Chem(合成化学),2012,20:7-12.
    [4]
    Chen LW,Zhang HB,Liang HX,et al.Synthesis of sitafloxacin[J].Chin J Pharm(中国医药工业杂志).2014,45(1):1-4.
    [5]
    Hayakawa I,Atarashi S,Imamura M,et al. Preparation of 7-(azaspiroalkanyl)quinolonecarboxylates and analogs as bactericides:CN,1040790[P].1990-03-28.
    [6]
    Akiba T,Ebata T,Saito T,et al.Processes for preparing cyclic compounds:CN,1191529[P].1998-08-26.
    [7]
    Nakayama K,Muto M,Saito T,et al.Processes for preparation of bicyclic compounds(aminoazaspiroalkanes)and intermediates therefor:CN,1293054[P].2007-01-03.
    [8]
    Nakayama K,Muto M,Saito T,et al.Processes for preparation of bicyclic compounds(aminoazaspiroalkanes)and intermediates therefor:CN,100473645[P].2009-04-01.
    [9]
    Satoh K,Imura A,Miyadera A,et al.An Efficient synthesis of key intermediate of Du-6859a via asymmetric microbial reduction[J].Chem Pharm Bull,1998,46(4):587-590.
    [10]
    Daniel JP,Steven AK,Frederick AP,et al.Enantioselective synthesis of 3-aminopyrrolidines:US,6197974B1[P].2001-03-06.
    [11]
    Yao Y,Fan W,Li W,et al.Synthesis of(S)-7-amino-5-azaspiro[2.4] heptane via highly enantioselective hydrogenation of protected ethyl 1-(2-aminoaceto)cyclopropanecarboxylates[J].J Org Chem,2011,76(8):2 807-2 813.
    [12]
    Chakraborty TK,Azhar Hussain K,Venkat Reddy G.α-Phenylglycinol as chiral auxiliary in diastereoselective strecker synthesis of α-amino acids[J].Tetrahedron,1995,51(33):9 179-9 190.
    [13]
    Sun H,Xu L.Preparation of optically active cyclic compound: CN,103012198[P].2013-04-03.
  • Related Articles

    [1]ZANG Yunna, SUN Jianguo, A Jiye, ZHAO Yuqing, JIN Xiaoliang, WANG Guangji. Stereoselective pharmacokinetics of itraconazole enantiomers in rats[J]. Journal of China Pharmaceutical University, 2015, 46(3): 339-344. DOI: 10.11665/j.issn.1000-5048.20150313
    [2]DONG Xiaoyang, WANG Ziyu, WANG Yongchao, DAI Zhenya, YOU Qidong. Recent progress in asymmetric organocatalysis and its applications in drug synthesis[J]. Journal of China Pharmaceutical University, 2013, 44(3): 193-201. DOI: 10.11665/j.issn.1000-5048.20130301
    [3]Two step process for diketoreduction catalyzed by diketoreductase[J]. Journal of China Pharmaceutical University, 2010, 41(5): 408-413.
    [4]Attempted asymmetric synthesis of optically pure tetrabenazine[J]. Journal of China Pharmaceutical University, 2010, 41(4): 321-325.
    [5]Novel evaluation theories of kinetics for controlled-release drug delivery systems[J]. Journal of China Pharmaceutical University, 2008, 39(1): 60-63.
    [7]Synthesis of Ethyl(3R,4R,5S)-4,5-epoxy-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate[J]. Journal of China Pharmaceutical University, 2003, (6): 101-102.
    [8]Asymmetric Synthesis of6-Fluoro-L-DOPA[J]. Journal of China Pharmaceutical University, 2001, (3): 8-13.
    [9]Asymmetric Reduction of Prochiral Ketones Using Chirally Modified Sodium Borohydride[J]. Journal of China Pharmaceutical University, 2000, (5): 7-9.
    [10]Asymmetric Cyclization Using Rhodium(I)with Chiral Ligand[J]. Journal of China Pharmaceutical University, 1995, (6): 324-328.

Catalog

    Article views (1094) PDF downloads (1867) Cited by()

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return