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Two optimized synthetic pathways toward a chiral precursor of Mivacurium chloride and other skeletal muscle relaxants
- 1.0425876 - MBÚ 2014 RIV GB eng J - Journal Article
Vilhanová, B. - Matoušek, V. - Václavík, J. - Syslová, K. - Přech, J. - Pecháček, J. - Šot, P. - Januščák, J. - Toman, J. - Zápal, Jakub - Kuzma, Marek - Kačer, P.
Two optimized synthetic pathways toward a chiral precursor of Mivacurium chloride and other skeletal muscle relaxants.
Tetrahedron Asymmetry. Roč. 24, č. 1 (2013), s. 50-55. ISSN 0957-4166
R&D Projects: GA ČR GA104/09/1497; GA ČR GAP106/12/1276
Institutional support: RVO:61388971
Keywords : ASYMMETRIC TRANSFER HYDROGENATION * IMINES * AGENTS
Subject RIV: CA - Inorganic Chemistry
Impact factor: 2.165, year: 2013
A chiral precursor of Mivacurium chloride, (R)-5'-methoxylaudanosine, was prepared using two different methods. The chiral resolution of racemic 5'-methoxylaudanosine, typically used in industry, was carried out in parallel with a procedure consisting of asymmetric transfer hydrogenation (ATH) and reductive methylation. A novel one-pot synthetic step was developed for the synthesis of racemic 5'-methoxylaudanosine. In both routes, the enantioselectivity was high but further purification was necessary to reach the level of a pharmaceutical standard. The individual synthetic steps reported herein can also be used for the synthesis of analogous bistetrahydroisoquinoline-based skeletal muscle relaxants.
Permanent Link: http://hdl.handle.net/11104/0231661
Number of the records: 1