Abstract
Reactive organometallics of lithium and magnesium are common intermediates in standard organic synthesis. As well, these reagents have been applied early and frequently in the synthesis of radiopharmaceuticals particularly in their labeling with short lived positron emitting isotopes. Reagents consisting of alkyl, cycloalkyl and aryl carbanions, α-amino-carbanions, anions of α-nitroalkanes, isocyanates, isonitriles and thioketals are among the useful. Reaction of these organometallics with eager or reluctant electrophiles such as CO2, CH3I, CO, F2, AcOF, RfOF, FCl03, etc. provide a diverse battery of synthetic approaches for the radiopharmaceutical chemist.
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References
Andersson Y, Malmborg P and Langstrom B. The Use of Organometallic Compounds in Synthesis of 11C-Labelled Aromatics. 8th Int Symp Radiopharm Chem. 1990, 141.
Lasne MC, Barre L, Piarraud A, Lalaoui K, Giroux B and Derlon JM. Synthesis of “No-Carrier Added ” Carbon-11 Fotemustine. 8th Int Symp Radiopharm Chem. 1990, 457.
Kiesewetter DO. Synthesis of 11C and 18F-Labelled Compounds for Receptor Research with PET. 197th American Chemical Society National Meeting. April 9–14, 1989, Dallas, Texas (Abstract).
Langstrom B and Sjoberg A. The Synthesis of Aliphatic and Aromatic Hydrocarbons Containing Methyl Groups Labelled with 11C. J Labelled Comp Radiopharm. 1981, 28, 671–682.
Kihlberg T, Malmborg P and Langstorm B. Syntheses of [L11C]-Labelled Fatty Acids Using Alkyl Halides and Grignard Reagents. 8th Int Symp Radiopharm Chem. 1990, 149.
Reiffers S, Vaalburg W, Widgman T, Wynberg H and Woldring MG. Carbon-11 Labelled Methyllithium as a Methyl Donating Agent: The Addition to 17-Keto Steroids. Int J Appl Radiat Isot. 1980, 31, 535–539.
Halldin C, Schoeps K-O, Ram S and Ehrenkaufer R. A Method for Preparation of (2-C-11)Amino Acids from (C-11)Nitroalkanes-Exemplified with (2-C-11)Glycine. Journal of Nuclear Medicine 1989, 30, 783 (Abstract).
Schoeps K-O, Halldin C, Stone-Elander S, Langstrom B and Greitz T. Preparation of 11C-Nitromethane and an Example of its Use as a Radiolabeling Precursor. J Labelled Comp Radiopharm. 1988, 25, 749–758.
Schoeps K-O, Stone-Elander S and Halldin C. On-Line Synthesis of [11C]Nitroalkanes. Appl Radiat Isot. 1989, 40, 261–262.
McPherson DW, Hwang D-R, Fowler JS, Wolf AP, MacGregor RR and Arnett CD. A Simple One-Pot Synthesis of Cyclopropane [11C]Carbonyl Chloride. Synthesis and Biodistribution of [11C]Cyclorphan. J Labelled Comp Radiopharm. 1986, 23, 505–514.
Luthra SK, Le Bars D, Pike VW, and Brady F. Preparation of NCA [1–11C]Acid Chlorides as Labelling Agents for Amides. J Labelled Comp Radiopharm. 1988, 26, 66–68.
Yorke JC Prenant C and Crouzel C. Synthesis of Carbon-11 Labelled Cyclopentyltheophylline: A Radioligand for PET Studies of Adenosine Receptors. 8th Int Symp Radiopharm Chem. 1990, 269.
Fasth KJ, Malmborg P and Langstrom B. Synthesis of Some 11C-Labelled Substituted Benzyl Iodides. J Labelled Comp Radiopharm. 1988, 26, 251–252.
Halldin C and Langstrom B. Synthesis of Racemic [311C]Phenylalanine and [3–11C]DOPA. Int J Appl Radiat Isot. 1984, 35, 779–782.
Halldin C and Langstrom B. Asymmetric Synthesis of L-[3–11C] Phenylalanine Using Chiral Hydrogenation Catalysts. Int J Appl Radiat Isot. 1984, 35, 945–948.
Kilbourn MR, Dischino DD and Welch MJ. Synthesis of DL-[311C]Phenylalanine. Int J Appl Radiat Isot. 1984, 35, 603605.
Lasne MC, Cairon P, Barre L, Moreau B and Pike VW. Preparation of N.C.A. [11C]Acrylic Derivatives for [11C] Allylation of Amines. 8th Int Symp Radiopharm Chem. 1990, 125.
Ehrin E, Luthra SK, Crouzel C, Pike VW. Preparation of Carbon-11 Labelled Prazosin, A Potent and Selective A1Adrenoreceptor Antagonist. J Labelled Comp Radiopharm. 1988, 25, 177–183.
LeBars D, Luthra SK, Pike VW and Swenson ER. Appl Radiat Isot. 1989, 39, 671.
Fasth KJ, Antoni G, Malmborg P and Langstrom B. Asymmetric Synthesis of 11C-Labelled Amino Acids. J Labelled Comp Radiopharm. 1988, 26, 88–89.
Langstrom B, Malmborg P and Fasth KJ. Two Synthetic Routes for the Asymmetric Synthesis of [0_11c] Amino Acids with High Enantiometric Purities. 8th Int Symp Radiopharm Chem. 1990, 411.
Langstrom B, Antoni G, Gullberg P, et al. The Synthesis of 1–11C-Labeled Ethyl, Propyl, Butyl and Isobutyl Iodides and Examples of Alkylation Reactions. Appl Radiat Isot. 1986, 37, 1141–1145.
Schoeps K-O, Halldin C, Thorell J-O, Stone-Elander S, Blomqvist G and Widen L. On-Line Production of 11CNitroalkanes and the Use of [11C]Nitromethane in the synthesis of D-[1–11C]Glucose. J Labelled Comp Radiopharm. 1988, 26, 86–87.
Berger G, Maziere M, Prenant C and Comar D. Synthesis of Carbon-11 Labelled Acetone. Int J Appl Radiat Isot. 1980, 31, 577–578.
Nagren K and Langstrom B. A Comparative Study on the Reaction of 11CO2 with Alkyl Metal Reagents. J Labelled Comp Radiopharm. 1988, 26, 83–85.
Prenant C and Crouzel C. Synthesis of n.c.a [11C]Sarin. J Labelled Comp Radiopharm. 1988, 26, 405–406.
Antoni G and Langstrom B. Synthesis of D,L-[3–11C] Valine Using [2–11C] Isopropyl Iodide, and Preparation of L-[3–11C] Valine by Treatment with D-Amino Acid Oxidase. Appl Radiat Isot. 1987, 38, 655.
Stone-Elander S, Roland P, Halldin C, Schwenner E, Boeshagen H and Widen L. Synthesis of [11C]Sodium Thiocyanate and [Isopropyl-11C]Nimodipine for the In Vivo Study of Ion Channels Using PET. J Labelled Comp Radiopharm. 1988, 26, 238–239.
Bolster JM, Vaalburg W, Elsinga H, Woldring MG and Wynberg H. Synthesis of Carbon-11 Labelled Glycine and the Dipeptides L-Phenylalanylglycine and L-Leucylglycine. Appl Radiat Isot. 1986, 37, 985–987.
Bolster JM, Hoeve WT, Vaalburg W, Van Dijk TH, Zijlstra JB, Paans AMJ, Wynberg H and Woldring MG. The Preparation of Carbon-11 Labelled Proline for Positron Emission Tomography. Preliminary Distribution Studies in Rats with Walker 256 Carcinosarcoma. Int J Appl Radiat Isot. 1985, 36, 339–343.
Ram S, Ehrenkaufer RE and Jewett DM. Rapid ReductiveCarboxylation of Secondary Amines, One-Pot Synthesis of N’(4–11C-Methyl)Imipramine. Appl Radiat Isot. 1986, 37, 39 1395.
Prenant C, Barre L and Crouzel C. Synthesis of [11C]-3Quinuclidinylbenzilate (QNB). J Labelled Comp Radiopharm. 1989, 27, 1257–1273.
Imahori Y, Fujii R, Ido T, Hirakawa K, Nakahashi H. Positron Labeled Phorbol Ester: Synthesis Method for “No-Carrier Added” Phorbol 13-[1–11C]Butyrate Using Ketene Reaction. J Labelled Comp Radiopharm. 1989, 27, 1025–1034.
Kilbourn MR Jerabek PA and Welch MJ. Synthesis of Carbon-11 Labeled Amides Via Carbonylation of Lithium Dialkylamides. Chem. Commun. 1983, 861.
Lerman O and Rozen S. Acetyl Hypofluorite, A New Moderating Carrier of Elemental Fluorine and Its Use in Fluorination of 1,3-Dicarbonyl Derivatives. J Org Chem. 1983, 48, 724–727.
Rozen S and Hebel D. Acyl Hypofluorites. A New Class of Organic Compounds. J Org Chem. 1990, 55, 2621–2623.
Mulholland GK and Ehrenkaufer RE. Facile, Temperature-Dependent Formation of Gaseous C1 and C2 Perfluoroalkyl Hypofluorites. Applications as Electrophilic Fluorinating Agents. J Org Chem. 1986 51, 1482–1489.
Rozen S, Brand M. Director Fluorination of Lithium Enolates with Acetyl Hypofluorite. Synthesis 1985, 665–667.
Ehrenkaufer RE and MacGregor RR. Synthesis of [18F]Perchloryl Fluoride and its Reactions with Functionalized Aryl Lithiums. Int J Appl Radiat Isot. 1983, 34, 613–615.
Oberdorfer F, Hofmann E and Maier-Borst W. Preparation of 18F-Labelled N-Fluoropyridinium Triflate. J Labelled Comp Radiopharm. 1988, 25, 999–1005.
Umemoto T, Kawada K and Tornita K. N-Fluoropyridinium Triflate and Its Derivatives: Useful Fluorinating Agents. Tetrahedron Letters 1986, 37, 4465–4468.
Bank RE, Du Boisson RA and Tsiliopoulos E. Electrophilic Fluorination with N-Fluoroquinuclidinium Fluoride. J Fluor Chem. 1986, 32, 461–466.
Singh S, DesMarteau DD, Zuberi SS, Witz M and Huang H-N. NFluoroperfluoroalkylsulfonimides. Remarkable New Fluorination Reagents. J Am Chem Soc. 1987, 109, 7194–7196.
Tee OS, Iyengar NR and Paventi M. 1-Fluoro-2-pyridone: A Useful Fluorinating Reagent. J Org Chem. 1983, 48, 761–762.
Satyamurthy N, Bida GT, Phelps ME and Barrio JR. NFluorolactams: Rapid, Mild, and Regiospecific Fluorinating Agents. J Org Chem. 1990, 55, 3373–3374.
Barnette WE. N-Fluoro-N-alkylsulfonamides: Useful Reagents for the Fluorination of Carbanions. J Am Chem Soc. 1984 106, 452–454.
Fellers TL, Hofmann E, Oberdorfer F and Maier-Borst W. Preparation and Characterization of 18F Labelled N-Fluoro Compounds as Electrophilic Labelling Reagents. J Labelled Comp Radiopharm. 1989, 26, 8–9.
Satyamurthy N, Bida GT, Barrio, JR, Phelps, ME. [18F]NFluoro-N-alkyl-sulfonamides: Novel Reagents for Radiofluorination. J Nucl Med. 1984, 25, P23 (Abstract).
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Ehrenkaufer, R.E., Scripko, J.G. (1991). Use of Organolithium and Organomagnesium Reagents in Radiopharmaceutical Synthesis. In: Emran, A.M. (eds) New Trends in Radiopharmaceutical Synthesis, Quality Assurance, and Regulatory Control. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-0626-7_24
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DOI: https://doi.org/10.1007/978-1-4899-0626-7_24
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