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Regioselective ring opening of 2-methylaziridine derivatives with F- and F-fluoride |
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| Authors: | Erik M van Oosten Michael GerkenPaul Hazendonk Roxanne ShankSylvain Houle Alan A Wilson Neil Vasdev |
| Institution: | a PET Centre, Centre for Addiction and Mental Health, Toronto, ON, Canada M5T 1R8 b Department of Chemistry, University of Toronto, Toronto, ON, Canada M5S 3H6 c Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, Canada T1K 3M4 d Department of Psychiatry, University of Toronto, Toronto, ON, Canada M5T 1R8 |
| Abstract: | Regioselectivity of the nucleophilic ring opening of N-benzoyl (Bz) and N-benzyloxycarbonyl (Cbz) activated 2-methylaziridines with anhydrous tetramethylammonium fluoride, anhydrous hydrogen fluoride, and 19F or 18F]-labelled potassium cryptand fluoride (K222]18/19F]) were investigated. Whereas all reactions with rigorously anhydrous N(CH3)4F did not ring-open the aziridines, reactions with anhydrous HF exclusively yielded the 2-fluoropropanamine derivatives. Reactions of Bz-protected and Cbz-protected 2-methylaziridine with K222]18/19F] yielded the 2-fluoropropanamine and 1-fluoro-2-propanamine derivatives as the major products, respectively, and represents the first example of regiocontrol during ring opening of aziridines with 18F]-fluoride. |
| Keywords: | Aziridine Fluorine-18 Ring opening Fluoroamines |
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