首页 | 本学科首页   官方微博 | 高级检索  
     


The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine: a key intermediate for the preparation of SIB-1508Y
Affiliation:1. Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Kanakapura, Bangalore 562112, Karnataka, India;2. Pilot Plant Development and Training Institute, King Mongkut’s University of Technology Thonburi, Bangkhuntien-Chaitalay Road, Thakam, Bangkok 10150, Thailand;1. Institute of Chemistry, The Jan Kochanowski University, Swietokrzyska 15G, 25-406 Kielce, Poland;2. Institute of Chemistry, Faculty of Food Technology, University of Agriculture, Balicka St. 122, 31-149 Kraków, Poland;3. Institute of Physics, The Jan Kochanowski University, Swietokrzyska 15G, 25-406 Kielce, Poland;1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, 710127 Xi’an, Shaanxi, P. R. China;2. Department of Chemistry, University of Houston-Clear Lake, 77058-1002 Houston, TX, USA;3. College of Materials and Chemical Engineering, Research Institute of Materials, China Three Gorges University, 443002 Yichang, Hubei, P. R. China;1. Division of Chemistry, Bialystok University of Technology, Zamenhofa 29, 15-435 Bialystok, Poland;2. Institute of Chemistry, University of Bialystok, Hurtowa 1, 15-399 Bialystok, Poland
Abstract:The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine is described via intramolecular hydroboration–cycloalkylation of an azido-olefin intermediate. The chiral homoallylic alcohol was efficiently synthesized by enantioselective reduction of the corresponding ketone using (+)-diisopinocamphenylchloroborane as the key reaction. The total synthesis of (S)-SIB-1508Y was achieved with an enantiomeric excess (e.e.) of 94% in ten steps and in 18% overall yield from the commercially available 5-bromo-3-pyridinecarboxylic acid.
Keywords:
本文献已被 ScienceDirect 等数据库收录!
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号