Home

Citation: SONG Guang-Wei, ZHU Jin-Tao, YAO Guo-Xin, CHEN Gang. Asymmetric Synthesis of (S)-Metoprolol[J]. Chinese Journal of Applied Chemistry, ;2010, 27(11): 1286-1290. doi: 10.3724/SP.J.1095.2010.90880 shu

Asymmetric Synthesis of (S)-Metoprolol

Department of Chemistry, Zhejiang Science-Technology University, Hangzhou 310018

Received Date: 25 December 2009
Revised Date: 19 March 2010

Enantioenriched(S)-3-chloro-1,2-propanediol and(R)-epichlorohydrin were obtained from the kinetic hydrolysis resolution of racemic epichlorohydrin by(S,S)-salen Co(Ⅲ) OAc.(S)-Metoprolol with optical purity higher than 99% could be prepared via the reaction of 4-(2-methoxyethyl) phenol with(S)-3chloro-1,2-propanediol followed by an amination reaction using isopropyl amine.When (R)-epichlorohydrin was used as the chiral precursor,(S)-metoprolol could be also prepared but with less optical purity(>92%). The overall yield of(S)-metoprolol was 53.9%.The structure of the product was determined by IR,¹H NMR,¹³C NMR and MS.This procedure is effective,simple and has a high utilization rate of raw material.The optical purity and yield of the product are satisfactory.The process is promising for scaling-up industrial potential applications.
- (S)-metoprolol,
- racemic epichlorohydrin,
- catalyzed hydrolysis resolution,
- (R)-epichlorohydrin,
- (S)-chloropropanediol,
- asymmetric synthesis
1. [1]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
2. [2]
  Lanjun Cheng , Xinyuan Wang , Jie An , Xiang Wu , Chengfeng Zhu , Yanming Fu , Yougui Li . Improvement of the Resolution Experiment of Racemic Tartaric Acid. University Chemistry, 2025, 40(7): 277-285. doi: 10.12461/PKU.DXHX202408010
3. [3]
  Qi Wang , Yuqing Liu , Jiefei Wang , Yuan-Yuan Ma , Jing Du , Zhan-Gang Han . Catalysts for electrocatalytic dechlorination of chlorinated aromatic hydrocarbons: synthetic strategies, applications, and challenges. Acta Physico-Chimica Sinica, 2025, 41(10): 100120-0. doi: 10.1016/j.actphy.2025.100120
4. [4]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
5. [5]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
6. [6]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
7. [7]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
8. [8]
  Shiyi Chen , Jialong Fu , Jianping Qiu , Guoju Chang , Shiyou Hao . Waste medical mask-derived carbon quantum dots enhance the photocatalytic degradation of polyethylene terephthalate (PET) over BiOBr/g-C₃N₄ S-scheme heterojunction. Acta Physico-Chimica Sinica, 2026, 42(1): 100135-0. doi: 10.1016/j.actphy.2025.100135
9. [9]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
10. [10]
  Deyun Ma , Fenglan Liang , Qingquan Xue , Yanping Liu , Chunqiang Zhuang , Shijie Li . Interfacial engineering of Cd_0.5Zn_0.5S/BiOBr S-scheme heterojunction with oxygen vacancies for effective photocatalytic antibiotic removal. Acta Physico-Chimica Sinica, 2025, 41(12): 100190-0. doi: 10.1016/j.actphy.2025.100190
11. [11]
  Jinwang Wu , Qijing Xie , Chengliang Zhang , Haifeng Shi . Rationally Designed ZnFe_1.2Co_0.8O₄/BiVO₄ S-Scheme Heterojunction with Spin-Polarization for the Elimination of Antibiotic. Acta Physico-Chimica Sinica, 2025, 41(5): 100050-0. doi: 10.1016/j.actphy.2025.100050
12. [12]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
13. [13]
  Jiali Lei , Juan Wang , Wenhui Zhang , Guohong Wang , Zihui Liang , Jinmao Li . TiO₂/CdIn₂S₄ S-scheme heterojunction photocatalyst promotes photocatalytic hydrogen evolution coupled vanillyl alcohol oxidation. Acta Physico-Chimica Sinica, 2025, 41(12): 100174-0. doi: 10.1016/j.actphy.2025.100174
14. [14]
  Yadan Luo , Hao Zheng , Xin Li , Fengmin Li , Hua Tang , Xilin She . Modulating reactive oxygen species in O, S co-doped C₃N₄ to enhance photocatalytic degradation of microplastics. Acta Physico-Chimica Sinica, 2025, 41(6): 100052-0. doi: 10.1016/j.actphy.2025.100052
15. [15]
  Yinjie Xu , Suiqin Li , Lihao Liu , Jiahui He , Kai Li , Mengxin Wang , Shuying Zhao , Chun Li , Zhengbin Zhang , Xing Zhong , Jianguo Wang . Enhanced Electrocatalytic Oxidation of Sterols using the Synergistic Effect of NiFe-MOF and Aminoxyl Radicals. Acta Physico-Chimica Sinica, 2024, 40(3): 2305012-0. doi: 10.3866/PKU.WHXB202305012
16. [16]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
17. [17]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-0. doi: 10.3866/PKU.WHXB202312024
18. [18]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
19. [19]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . Performance and Electrochemical Asymmetry Optimization of Hydrogen Electrode Supported Reversible Solid Oxide Cell. Acta Physico-Chimica Sinica, 2025, 41(1): 100005-0. doi: 10.3866/PKU.WHXB202309037
20. [20]
  Shumin Zhang , Yaqi Wang , Zelin Wang , Libo Wang , Changsheng An , Difa Xu . Ultrafast electron transfer at the ZIS_1−x/UCN S-scheme interface enables efficient H₂O₂ photosynthesis coupled with tetracycline degradation. Acta Physico-Chimica Sinica, 2025, 41(11): 100136-0. doi: 10.1016/j.actphy.2025.100136

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(468)
HTML views(32)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return