Synthesis, Inhaltsverzeichnis Synthesis 2017; 49(09): 2057-2062DOI: 10.1055/s-0036-1588133 paper © Georg Thieme Verlag Stuttgart · New YorkA Borrowing Hydrogen Approach to the Synthesis of RS-67,333 Elodie Carbonnel VFP Therapies, R & D Laboratory, IRCOF, Rue Tesnière, 76131 Mont Saint Aignan, France eMail: vgembus@vfp-therapies.com , Florent Alix VFP Therapies, R & D Laboratory, IRCOF, Rue Tesnière, 76131 Mont Saint Aignan, France eMail: vgembus@vfp-therapies.com , Vincent Gembus* VFP Therapies, R & D Laboratory, IRCOF, Rue Tesnière, 76131 Mont Saint Aignan, France eMail: vgembus@vfp-therapies.com› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A new strategy using the borrowing hydrogen methodology to access the 5-HT4R agonist RS-67,333 is presented. Especially, this selective and highly potent ligand of 5-HT4 receptor was obtained quickly and efficiently by catalytic alkylation of a ketone with various alcohols in the presence of a catalytic amount of (Cp*IrCl2)2. Key words Key wordsiridium - catalysis - hydrogen transfer - alcohols - heterocycles Volltext Referenzen References 1a Meltzer CC, Smith G, DeKosky ST, Pollock BG, Mathis CA, Moore RY, Kupfer DJ, Reynolds CF. Neuropsychopharmacology 1998; 18: 407 1b Reynolds GP, Mason SL, Meldrum A, De Keczer S, Parnes H, Eglen RM, Wong EH. F. Br. J. Pharmacol. 1995; 114: 993 1c Bockaert J, Ansanay H, Waeber C, Sebben M, Fagni L, Dumuis A. CNS Drugs 1994; 1: 6 Selected references: 2a Darcet F, Gardier AM, David DJ, Guilloux J.-P. Neurosci. Lett. 2016; 616: 197 2b Claeysen S, Bockaert J, Giannoni P. ACS Chem. Neurosci. 2015; 6: 940 2c Quiedeville A, Boulouard M, Hamidouche K, Da Silva Costa-Aze V, Nee G, Rochais C, Dallemagne P, Fabis F, Freret T, Bouet V. Behav. Brain Res. 2015; 293: 10 2d Giannoni P, Gaven F, de Bundel D, Baranger K, Marchetti-Gauthier E, Roman FS, Valjent E, Marin P, Bockaert J, Rivera S, Claeysen S. Front. Aging Neurosci. 2013; 5: 96 2e Freret T, Bouet V, Quiedeville A, Nee G, Dallemagne P, Rochais C, Boulouard M. Behav. Brain Res. 2012; 230: 304 2f Marchetti E, Chaillan FA, Dumuis A, Bockaert J, Soumireu-Bourat B, Roman FS. Neuropharmacology 2004; 47: 1021 2g Lelong V, Lhonneur L, Dauphin F, Boulouard M. Naunyn-Schmiedebergs Arch. Pharmacol. 2003; 367: 621 2h Lamirault L, Guillou C, Thal C, Simon H. Prog. Neuropsychopharmacol. Biol. Psychiatry 2003; 27: 185 2i Moser PC, Bergis OE, Jegham S, Lochead A, Duconseille E, Terranova JP, Caille D, Bergue-Bestel I, Lezoualc’h F, Fischmeister R, Dumuis A, Bockaert J, George P, Soubrié P, Scatton B. J. Pharmacol. Exp. Ther. 2002; 302: 731 2j Robert SJ, Zugaza JL, Fischmeister R, Gardier AM. J. Biol. Chem. 2001; 276: 44881 2k Marchetti E, Dumuis A, Bockaert J, Soumireu-Mourat B, Roman FS. Neuropharmacology 2000; 39: 2017 2l Galeotti N, Ghelardini C, Bartolini A. J. Pharmacol. Exp. Ther. 1998; 286: 1115 2m Consolo S, Arnaboldi S, Giorgi S, Russi G, Ladinsky H. Neuroreport 1994; 5: 1230 3 Eglen RM, Bonhaus DW, Johnson LG, Leung E, Clark RD. Br. J. Pharmacol. 1995; 115: 1387 4 Lecoutey C, Hedou D, Freret T, Giannoni P, Gaven F, Since M, Bouet V, Ballandonne C, Corvaisier S, Malzert-Fréon A, Mignani S, Cresteil T, Boulouard M, Claeysen S, Rochais C, Dallemagne P. Proc. Natl. Acad. Sci. U.S.A. 2014; 111: E3825 5 Lucas G, Rymar VV, Du J, Mnie-Filali O, Bisgaard C, Manta S, Lambas-Senas L, Wiborg O, Haddjeri N, Pineyro G, Sadikot AF, Debonnel G. Neuron 2007; 55: 712 6 Clark RD, Jahangir A, Langston JA, Weinhardt KK, Miller AB, Miller AB, Leung E, Eglen RM. Bioorg. Med. Chem. Lett. 1994; 4: 2477 7 Clark RD, Eglen R, Jahangir A, Miller AB, Gardner JO. Patent PCT Int. Appl. WO 1994027965 A1, 1994 8 Rochais C, Lecoutey C, Gaven F, Giannoni P, Hamidouche K, Hedou D, Dubost E, Genest D, Yahiaoui S, Freret T, Bouet V, Dauphin F, Sopkova de Oliveira Santos J, Ballandonne C, Corvaisier S, Malzert-Fréon A, Legay R, Boulouard M, Claeysen S, Dallemagne P. J. Med. Chem. 2015; 58: 3172 Selected reviews: 9a Yang Q, Wang Q, Yu Z. Chem. Soc. Rev. 2015; 44: 2305 9b Obora Y. ACS Catal. 2014; 4: 3972 9c Gunanathan C, Milstein D. Science 2013; 341: 249 9d Dobereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681 9e Pan S, Shibata T. ACS Catal. 2013; 3: 704 9f Guillena G, Ramón DJ, Yus M. Angew. Chem. Int. Ed. 2007; 46: 2358 9g Hamid MH. S. A, Slatford PA, Williams JM. J. Adv. Synth. Catal. 2007; 349: 1555 9h Fujita KI, Yamaguchi R. Synlett 2005; 560 Selected references: 10a Huang F, Liu Z, Yu Z. Angew. Chem. Int. Ed. 2016; 55: 862 10b Elangovan S, Sortais J.-P, Beller M, Darcel C. Angew. Chem. Int. Ed. 2015; 54: 14483 10c Li F, Ma J, Wang J. J. Org. Chem. 2014; 79: 10447 10d Martínez R, Ramón DJ, Yus M. Tetrahedron 2006; 62: 8988 10e Kwon MS, Kim N, Seo SH, Park IS, Cheedrala RK, Park J. Angew. Chem. Int. Ed. 2005; 44: 6913 10f Fujita K.-I, Asai C, Yamaguchi T, Hanasaka F, Yamaguchi R. Org. Lett. 2005; 7: 4017 10g Taguchi K, Nakagawa H, Hirabayashi T, Sakaguchi S, Ishii Y. J. Am. Chem. Soc. 2004; 126: 72 Zusatzmaterial Zusatzmaterial Supporting Information
