3-Hydroxycyclopent-1-ene-1-carboxylic acid (HOCPCA (1)) is a potent ligand for high-affinity γ-hydroxybutyric acid binding sites in the central nervous system. Various approaches to the introduction of a hydrogen label onto the HOCPCA skeleton are reported. The outcomes of the feasible C─H activation of olefin carbon (C-2) by iridium catalyst are compared with the reduction of the carbonyl group (C-3) by freshly prepared borodeuterides. The most efficient iridium catalysts proved to be Kerr bulky phosphine N-heterocyclic species providing outstanding deuterium enrichment (up to 91%) in a short period of time. The highest deuterium enrichment (>99%) was achieved through the reduction of ketone precursor 2 by lithium trimethoxyborodeuteride. Hence, analogical conditions were used for the tritiation experiment. [3 H]-HOCPCA selectively labeled on the position C-3 was synthetized with radiochemical purity >99%, an isolated yield of 637 mCi and specific activity = 28.9 Ci/mmol.
- Klíčová slova
- C─H activation, borotritides, hydrogen/deuterium exchange, iridium catalyst, tritium-labeled γ-hydroxybutyric acid,
- MeSH
- alkeny chemie MeSH
- bor chemie MeSH
- deuterium chemie MeSH
- hydroxybutyráty chemie MeSH
- iridium chemie MeSH
- izotopové značení MeSH
- katalýza MeSH
- ligandy MeSH
- oxidace-redukce MeSH
- tritium chemie MeSH
- vodík-deuteriová výměna * MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- 4-hydroxybutyric acid MeSH Prohlížeč
- alkeny MeSH
- bor MeSH
- deuterium MeSH
- hydroxybutyráty MeSH
- iridium MeSH
- ligandy MeSH
- tritium MeSH
