247923-41-7Relevant articles and documents
Reaction development and mechanistic study of a ruthenium catalyzed intramolecular asymmetric reductive amination en route to the dual orexin inhibitor suvorexant (MK-4305)
Strotman, Neil A.,Baxter, Carl A.,Brands, Karel M. J.,Cleator, Ed,Krska, Shane W.,Reamer, Robert A.,Wallace, Debra J.,Wright, Timothy J.
, p. 8362 - 8371 (2011)
The first example of an intramolecular asymmetric reductive amination of a dialkyl ketone with an aliphatic amine has been developed for the synthesis of Suvorexant (MK-4305), a potent dual Orexin antagonist under development for the treatment of sleep di
Catalytic asymmetric Michael addition with curcumin derivative
Li, Wenjun,Wu, Wenbin,Yu, Feng,Huang, Huicai,Liang, Xinmiao,Ye, Jinxing
supporting information; experimental part, p. 2505 - 2511 (2011/05/06)
Catalytic asymmetric Michael additions with curcumin derivatives were achieved by a new series of tertiary amine-thiourea organocatalysts to afford the Michael adducts in high yields and excellent enantioselectivities.
Chemistry of opium alkaloids, 45. Improvements in the total synthesis of morphine
Meuzelaar, Gerrit J.,Van Vliet, Michiel C. A.,Maat, Leendert,Sheldon, Roger A.
, p. 2315 - 2321 (2007/10/03)
The chiral 1,2,3,4-tetrahydroisoquinoline intermediates in the Price and Beyerman routes to morphine, (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy- 1,2,3,4-tetrahydroisoquinoline (6) and (+)-(R)-1-(3,5-dibenzyloxy-4- methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (5), were prepared in high ee by ruthenium-catalyzed asymmetric transfer hydrogenation of the corresponding imine precursors (Noyori method). The yield of the key raw material in the Beyerman route, 3,5-dibenzyloxy-4-methoxyphenylacetric acid (1), starting from gallic acid methyl ester (7) was improved by a factor of 5 over previously described syntheses. Key steps in the new procedure are the selective formation of methyl 3,5-dihydroxy-4-methoxybenzoate (9) via the 3,5-diacetate and an improved benzylation of the hydroxyl groups in 9.