Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2119-2123.DOI: 10.6023/cjoc201404031 Previous Articles     Next Articles

Notes

雄甾-3,17-二醇衍生物的分子结构研究

方明锋a, 儲储刚b, 李歆a, 陆国元b,c   

  1. a. 南京林业大学化学工程学院 南京 210037;
    b. 南京圣和药业公司 南京 210038;
    c. 南京大学化学化工学院 南京 210093
  • 收稿日期:2014-04-17 修回日期:2014-06-01 出版日期:2014-10-25 发布日期:2014-06-18
  • 通讯作者: 方明锋, 陆国元 E-mail:hgfmf@njfu.edu.cn
  • 基金资助:

    国家自然科学青年基金(No. 31200451)、江苏省自然科学基金(No. BK2012821)、江苏高校优势学科建设工程资助项目.

Studies of Molecular Structures of 3,17-Androstandiol Derivative

Fang Mingfenga, Chu Gangb, Li Xina, Lu Guo Yuanb,c   

  1. a. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b. Sanhome Pharmaceutical Co., Ltd., Nanjing 210038;
    c. Department of Chemistry, Nanjing University, Nanjing 210093
  • Received:2014-04-17 Revised:2014-06-01 Online:2014-10-25 Published:2014-06-18
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31200451), the Natural Science Foundation of Jiangsu Province (No. BK2012821) and the Foundation of Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions.

Rocuronium bromide is a new neuromuscular blocking agent in clinical intervention. Its potency, specificity of action and little side effect have been confirmed. The 3,17-androstandiol (1) is a key intermediate for the preparation of rocuronium bromide. In this paper, The 3,17-androstandiol (1) was synthesized from (2α,3α,5α,16β)-2,3-epoxy-16- (1-pyrrolidinyl)-17-oxoandrostane by a reduction with sodium borohydride in methanol and then an epoxy ring opening reaction in morpholine and water. The molecular constitution was confirmed by 1H NMR, 13C NMR, 1H-1H COSY, DEPT, HSQC,HMBC, 2D NOESY and TOF-MS spectra. The single crystal of 3,17-androstandiol (1) was prepared by crystallized from 2-MeTHF and then was subjected to X-ray crystallography analysis that confirmed the stereo configuration of compound 1. And studies of X-ray powder diffractive analysis indicate that the diffractive spectrum of the sample compound 1 is consistent with the diffractive spectrum calculated on the crystal data. Therefore, the compound is (2β,3α,5α,16β,17β)- 2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstan-3,17-diol and its stereochemistry is accordant with that of rocuronium bromide.

Key words: androstandiol, rocuronium bromide, NMR spectra, configuration, crystal structure