Further Radiopharmaceuticals for Positron Emission Tomography and New Strategies for Their Production, Volume 2 (eBook)

Peter J. H. Scott is an Assistant Professor in the Department of Radiology at the University of Michigan Medical School (USA), Director of the University of Michigan PET Center (USA) and a member of the Interdepartmental Program in Medicinal Chemistry. Professor Scott edited Linker Strategies in Solid-Phase Organic Synthesis (also from Wiley) and is the series editor for both the Wiley Series on Radiochemical Syntheses and the Wiley Series on Solid Phase Organic Syntheses.

Contributors xi

Editorial Preface xvii

Abbreviations xix

PART I FLUORINE-18 LABELED RADIOPHARMACEUTICALS 1

1. Synthesis of (.)-[18F]Flubatine ([18F]FLBT) 3
Megan N. Stewart, Brian G. Hockley, and Peter J. H. Scott

2. Synthesis of [18F]-(.)Fluoroethoxy Benzovesamicol ([18F]FEOBV) 13
Brian G. Hockley, Megan N. Stewart, and Peter J. H. Scott

3. Synthesis of [18F]Fluoromethylcholine ([18F]FCH) via [18F]Fluoromethyl Tosylate 21
Melissa E. Rodnick, Allen F. Brooks, Brian G. Hockley, Bradford D. Henderson, and Peter J. H. Scott

4. Radiosynthesis of [18F]Flotegatide ([18F]RGD-K5) 29
Hartmuth C. Kolb, Fanrong Mu, Umesh Gangadharmath, Vani P. Mocharla, Zhihong Zhu, Ashok Chaudhary, and Joseph C. Walsh

5. Synthesis of 3-[18F]Fluoro-5-(2-Pyridinylethynyl) Benzonitrile ([18F]FPEB) 41
Steven H. Liang, Daniel L. Yokell, Raul N. Jackson, Peter A. Rice, Eli Livni, David Alagille, Gilles Tamagnan, Thomas Lee Collier, and Neil Vasdev

6. Radiosynthesis of 2'-Deoxy-2'-[18F]Fluoro-5-Methyl-1-ß-d-Arabinofuranosyluracil ([18F]FMAU) 53
Kai Chen and Peter S. Conti

PART II CARBON-11 LABELED RADIOPHARMACEUTICALS 63

7. Synthesis of N-[11C]Methyl-4-Piperidinyl Propionate ([11C]PMP) 65
Xia Shao and Peter J. H. Scott

8. Synthesis of 1-(2,4-Dichlorophenyl)-4-Cyano-5-(4-[11C]methoxyphenyl)-N-(Piperidin-1-yl)-1H-Pyrazole-3-Carboxamide ([11C]OMAR) 73
Xia Shao, Keunsam Jang, and Peter J. H. Scott

9. Synthesis of Carbon-11 Labeled (+)-4-Propyl-3,4,4a,5,6,10b-Hexahydro-2H-Naphtho[1,2-b][1,4]Oxazin-9-Ol ([11C]-(+)-PHNO) 81
Christophe Plisson, Joaquim Ramada-Magalhaes, and Jan Passchier

10. Synthesis of (R)-[N-Methyl-11C]PK11195 93
Vítor H. Alves, Antero J. Abrunhosa, and Miguel Castelo-Branco

PART III OTHER RADIOPHARMACEUTICALS 103

11. Synthesis of Oxygen-15 Water ([15O]H2O) 105
David W. Dick and G. Leonard Watkins

PART IV NEW METHODS FOR THE SYNTHESIS AND QUALITY CONTROL OF RADIOPHARMACEUTICALS 115

12. Direct, Nucleophilic Radiosynthesis of [18F]Trifluoroethyl Tosylate 117
Patrick J. Riss, Waqas Rafique, and Franklin I. Aigbirhio

13. Synthesis of [18F]N-Methyl Lansoprazole via Generation of a [18F]Trifluoromethyl Group 123
Allen F. Brooks, Melissa E. Rodnick, Garret M. Carpenter, and Peter J. H. Scott

14. [18F]Fluorination of (Mesityl)(Aryl)Iodonium Salts 129
Naoko Ichiishi, Allen F. Brooks, Joseph J. Topczewski, Melissa E. Rodnick, Melanie S. Sanford, and Peter J. H. Scott

15. Pd(IV)-Mediated Fluorination of Arenes with [18F]F- for PET Imaging 139
Nathan J. Schauer, Stephen M. Carlin, Hong Ren, and Jacob M. Hooker

16. Silicon Fluoride Acceptors (SIFAs) for Peptide and Protein Labeling with 18F 149
Ralf Schirrmacher, Alexey Kostikov, Carmen Wängler, Klaus Jurkschat, Vadim Bernard-Gauthier, Esther Schirrmacher, and Björn Wängler

17. Solid Phase Synthesis of [18F]-2-Fluoro-2-Deoxy-d-Glucose: A Resin-Linker-Vector (RLV) Approach 163
Lynda J. Brown, Imtiaz Khan, Harry J. Wadsworth, Alexander Jackson, Nianchun Ma, Nicolas Millot, Sue M. Champion, Denis R. Bouvet, Alex M. Gibson, and Richard C. D. Brown

18. Production and Reaction of [11C]Carbon Disulfide for the Synthesis of [11C]Dithiocarbamates 177
Philip W. Miller

19. One-Pot, Direct Incorporation of [11CO2] into Carbamates 185
Christian K. Moseley and Jacob M. Hooker

20. Radiosynthesis of [11C]Carboxamides via Reaction of [11C]CO2 Captured by a Cu(I)-Based Catalyst System with Boronic Acid Ester Precursors 197
Patrick J. Riss, Shuiyu Lu, Sanjay Telu, Franklin I. Aigbirhio, and Victor W. Pike

21. Ethanol as a Solvent for Carbon-11 Radiochemistry 207
Xia Shao, Maria V. Fawaz, Keunsam Jang, and Peter J. H. Scott

22. Synthesis and Applications of [11C]Hydrogen Cyanide 233
Xia Shao, Melissa E. Rodnick, Allen F. Brooks, and Peter J. H. Scott

23. Determination of Radiochemical Purity and Radiochemical Identity of [13N]NH3 Using Thin Layer Chromatography 241
Peter A. Rice and Daniel L. Yokell

Appendix 1: Supplier Information 247

Index 253