RPViewDoc - Radiolabelling with organomercury compounds...

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Radiolabelling with organomercury compounds. Part 1. The synthesis and structure of 6-halocholest-5-en-3P-01s RICHARD J. FLANAGAN, F. PETER CHARLESON, AND EYVIND 1. SYNNES Merck Frosst Canada IIIC., P.O. B0.r 1005, Pointe Claire - Dorval, P.Q. Catzada H9R 4P8 LEONARD 1. WIEBE YVON X. THERIAULT Faculty of Pharmacy and Pharmaceutical Sciences, Urliversity of Alberta, Edmonton, Alta., Canada T6G 2N8 THOMAS T. NAKASHIMA Department of Chemistry, University of Alberta, Ed~nontoti, Alm., Canada T6G 2N8 Received February 10, 1984 J. FLANAGAN, F. PETER CHARLESON, I. SYNNES, I. WIEBE, YVON X. THERIAULT, and THOMAS T. NAKASHIMA. Can. J. Chem. 63, 2853 (1985). The synthetic route to 6-chloromercuricholest-5-en-3~-ol has been studied and the yield improved from 2% to 20%. The reaction of 6-chloromercuricholest-5-en-3~-ol with fluorine, chlorine. bromine, and iodine has been examined. 6-Bromocholest-5-en-3P-ol and 6-chlorocholest-5-en-3P-01 have been directly prepared from 6-iodocholest-5-en-3P-ol using cuprous halides. A new intermediate, 6-tosyloxycholest-5-en-3P-01, has also been synthesized by the action of silver tosylate on 6-iodocholest-5-en-3P-01. The structures of the compounds were proven by a combination of high-resolution 'Hmr and "Cmr. A new crystal modification of 6-chloromercuricholest-5-en-3~-ol has been found. F. PETER CHARLESON, I. SYNNES, LEONARD I. WIEBE, YVON X. THERIAULT et THOMAS Can. J. Chem. 63, 2853 (1985). On a Ctudit la voie d'accks au chloromercuri-6 cholestene-5 01-3P et on a amCliorC le rendement de 2% B 20%. On a Ctudit la rkaction du chloromercuri-6 cholestkne-5 01-3P avec le fluor, le chlore, le brome et I'iode. Faisant appel B la reaction des halogCnures cuivreux avec I'iodo-6 cholestkne-5 ol-3P. on a rtalisC des syntheses directes des bromo-6 et chloro-6 cholostkne-5 01s-3P. On a Cgalement synthCtisC un nouvel intermtdiaire, le tosyloxy-6 cholestkne-5 01-3P, en faisant rkagir le tosylate d'argent sur I'iodo-6 cholestkne-5 01-3P. La rmn du 'H et du "C a haute rtsolution a permis d'Clucider les structures des composCs. On a trouvt une nouvelle modification cristalline du chloromercuri-6 cholestkne-5 01-3P. [Traduit par le journal] Introduction The need for high speed stereospecific methods for the intro- duction of radioligands into organic molecules has necessitated the development of novel synthetic methods. Some of the newer methods developed recently involve the reaction of se- lected organoboron (1-3), organotin (4), and organothallium compounds (5) with elemental iodine. We have chosen to ex- amine the feasibility of using organomercury compounds for this procedure. We felt that organomercury compounds offered a number of advantages over other organometallic inter- mediates in that they are easily accessible from organic halides, olefins, and aromatic amines. Such is not the case for organotin and especially organoboron compounds. Furthermore, organo- mercury compounds are known in the three common forms required for most labelling procedures, i.e. aliphatic, vinylic, and aromatic. We chose a vinyl organomercury compound as
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This note was uploaded on 02/17/2011 for the course CHEMISTRY 101 taught by Professor Csr during the Spring '11 term at University of Louisville.

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RPViewDoc - Radiolabelling with organomercury compounds...

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