24734-71-2Relevant academic research and scientific papers
Synthesis method of 5'-methoxyl laudanosine
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Paragraph 0035; 0040-0042; 0043; 0047-0048; 0049; 0053; ..., (2021/11/10)
The invention discloses a synthesis method of 5'-methoxyl laudanthin, belonging to the technical field of organic synthesis. According to the method, 3,4-dimethoxyphenylethylamine and 3,4,5-trimethoxyphenylacetaldehyde are used as initial raw materials through an optimized process by utilizing the Pictet-Spengler reaction, dichloromethane is used as a solvent, and under the catalysis of a transition metal lewis acid catalyst, a dehydration reaction is performed through a dehydrating agent at 23-27 DEG C, or refluxing is performed in formic acid and phosphorus pentoxide is used for dehydration; and synthesized 6,7-dimethoxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinen reacts with a methyl donor by using formic acid as a solvent to obtain 5'-methoxy laudanosine. According to a technical scheme in the invention, a synthetic route is short in step, toxic and harmful reagents including phosphorus oxychloride and methylbenzene are not used, the steps of hydrogenation reduction and the like are avoided, total reaction yield is high, the obtained 5'-methoxy laudanin is high in purity, process cost is low, a process is environmentally friendly, process operation is simple, and the method has actual production value and can be used for industrial production.
Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling
Lipp, Alexander,Selt, Maximilian,Ferenc, Dorota,Schollmeyer, Dieter,Waldvogel, Siegfried R.,Opatz, Till
supporting information, p. 1828 - 1831 (2019/03/07)
A fully regio- and diastereoselective electrochemical 4a-2′-coupling of a 3′,4′,5′-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone. This key intermediate is further transformed into (-)-oxycodone through conjugate nucleophilic substitution for E-ring closure and [4 + 2] cycloaddition with photogenerated singlet oxygen to accomplish diastereoselective hydroxylation at C-14. The anodic transformation provides high yields and can be performed under constant current conditions both in a simple undivided cell or in continuous flow.
Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis
Lipp, Benjamin,Lipp, Alexander,Detert, Heiner,Opatz, Till
, p. 2054 - 2057 (2017/04/27)
A light-induced C-C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp3)-C(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C(sp3)-C(sp3)-σ-bond rather than the well-known α-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.
Two optimized synthetic pathways toward a chiral precursor of Mivacurium chloride and other skeletal muscle relaxants
Vilhanová, Beáta,Matou?ek, Václav,Václavík, Ji?í,Syslová, Kamila,P?ech, Jan,Pechá?ek, Jan,?ot, Petr,Janu??ák, Jakub,Toman, Jaromír,Zápal, Jakub,Kuzma, Marek,Ka?er, Petr
, p. 50 - 55 (2013/02/23)
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
