A novel and practical asymmetric synthesis of dapoxetine hydrochloride

被引：7
|
作者：
Zhu, Yijun [1 ,2 ]
Liu, Zhenren [1 ]
Li, Hongyan [1 ]
Ye, Deyong [2 ]
Zhou, Weicheng [1 ]
机构：
[1] State Inst Pharmaceut Ind, Shanghai Key Lab Anti Infect, State Key Lab New Drug & Pharmaceut Proc, Shanghai 201203, Peoples R China
[2] Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 11卷
关键词：
asymmetric synthesis; dapoxetine hydrochloride; stereoselectivity; (S)-tert-butanesulfinamide; PREMATURE EJACULATION; (S)-DAPOXETINE;
D O I：
10.3762/bjoc.11.283
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and practical asymmetric synthesis of dapoxetine hydrochloride by using the chiral auxiliary (S)-tert-butanesulfinamide was explored. The synthesis was concise, mild, and easy to perform. The overall yield and stereoselectivity were excellent.
引用
收藏
页码：2641 / 2645
页数：5
相关论文
共 50 条
  • [41] A practical asymmetric synthesis of ortho-substituted 4-pyrazolyl-2-ethylamines
    O'Mahony, Donogh J. R.
    Johnson, Russell J.
    Estiarte, M. Angels
    Edwards, William T.
    Duncton, Matthew A. J.
    TETRAHEDRON LETTERS, 2019, 60 (47)
  • [42] Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (–)-menthol by Rh–BINAP catalysts
    Susumu Akutagawa
    Topics in Catalysis, 1997, 4 : 271 - 274
  • [43] Asymmetric synthesis of novel ferrocenyl ligands with planar and central chirality
    Enders, D
    Peters, R
    Lochtman, R
    Raabe, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (16) : 2421 - 2423
  • [44] Asymmetric synthesis of novel α-amino acids with β-branched side chains
    Zhang, Minsheng
    Porte, Alex
    Diamantidis, George
    Sogi, Kimberly
    Kubrak, Dennis
    Resnick, Lynn
    Mayer, Scott C.
    Wang, Zheng
    Kreft, Anthony F.
    Harrison, Boyd L.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) : 2401 - 2403
  • [45] Asymmetric synthesis of the cytotoxic lactone (+)-cardiobutanolide and two novel analogues
    Kovacevic, Ivana
    Popsavin, Mirjana
    Rodic, Marko V.
    Kojic, Vesna
    Popsavin, Velimir
    TETRAHEDRON LETTERS, 2019, 60 (09) : 684 - 687
  • [46] Mesoporous SiO2 (SBA-15) modified graphite electrode as highly sensitive sensor for ultra trace level determination of Dapoxetine hydrochloride drug in human plasma
    El-Desoky, Hanaa
    Abdel-Galeil, Mohamed
    Khalifa, Aya
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2019, 846
  • [47] Novel instantly-dispersible nanocarrier powder system (IDNPs) for intranasal delivery of dapoxetine hydrochloride: in-vitro optimization, ex-vivo permeation studies, and in-vivo evaluation
    Fouad, Shahinaze A.
    Shamma, Rehab N.
    Basalious, Emad B.
    El-Nabarawi, Mohamed M.
    Tayel, Saadi A.
    DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY, 2018, 44 (09) : 1443 - 1450
  • [48] Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids
    Soloshonok, VA
    Ueki, H
    Ellis, TK
    Yamada, T
    Ohfune, Y
    TETRAHEDRON LETTERS, 2005, 46 (07) : 1107 - 1110
  • [49] Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (-)-menthol by Rh-BINAP catalysts
    Akutagawa, S
    TOPICS IN CATALYSIS, 1997, 4 (3-4) : 271 - 274
  • [50] A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds
    Soloshonok, VA
    Cai, CZ
    Hruby, VJ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (12) : 2172 - +
12345