Synthesis of 6-(Fluoromethyl)-19-norcholest-5(10)-en-3-ol, a Fluorinated Analogue of NP-59, using the Mild Fluorinating Reagent, TBAF(Pinacol)2
| Autor: | Allen F. Brooks, Wade Winton, Benjamin L. Viglianti, Ka Kit Wong, Peter J. H. Scott |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Diethylamine
Pinacol Materials Science (miscellaneous) Organic Chemistry cholesterol Medicinal chemistry Catalysis fluorination Biomaterials Diethylaminosulfur trifluoride lcsh:Chemistry chemistry.chemical_compound Elimination reaction Silver fluoride chemistry pet adrenal lcsh:QD1-999 Yield (chemistry) Reagent Fluoride steroids |
| Zdroj: | SynOpen, Vol 03, Iss 02, Pp 55-58 (2019) |
| ISSN: | 2509-9396 |
| Popis: | For 45 years, efforts to prepare a fluorinated analogue of the scintiscanning/SPECT agent 6-(iodomethyl)-19-norcholest-5(10)-en-3-ol (NP-59) for development of a PET imaging agent have failed due to undesired elimination reactions and unexpected rearrangements observed while utilizing a wide variety of fluorinating conditions (e.g., cesium fluoride, silver fluoride, (2-chloro-1,1,2-trifluoroethyl)diethylamine (FAR), diethylaminosulfur trifluoride (DAST), and hexafluoropropene diethylamine FPA). Herein, we report the full synthesis of NP-59, followed by the four-step synthesis of 6-(fluoromethyl)-19-norcholest-5(10)-en-3-ol (FNP-59) using a recently developed mild fluorinating reagent, less prone to producing elimination reactions in the preparation of primary fluorides, TBAF(pinacol)2, with an overall yield of 16% (four steps). Also included is an evaluation of the TBAF(pinacol)2 reagent on eight test substrates to investigate its scope. |
| Databáze: | OpenAIRE |
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