Synthesis of deramciclane labelled with radiocarbon in various positions

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 39; no. 12; pp. 1011 - 1018
• Main Authors: Szammer, J, SimonTrompler, E, Mate, J, Abermann, M, Urmos, Klebovich
• Format: Journal Article
• Language: English
• Published: W SUSSEX Wiley 01.12.1997
• Subjects: Biochemical Research Methods; Biochemistry & Molecular Biology; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; [U-C-14-pheny]deramciclane; anxiolytic agents; carbon-14; 1R,2S,4R(-)-2-(dimethylaminoethoxy)-2-phenyl-1,7,7-trimethylbicyclo[2.2.1]heptane; [1-C-14-side chain]deramciclane
• ISSN: 0362-4803
• DOI: 10.1002/(SICI)1099-1344(199712)39:12<1011::AID-JLCR49>3.3.CO;2-Q

[U-C-14]Bromobenzene, prepared from [C-14]barium carbonate according to literature procedures, was transformed (Li/diethylether) into [C-14]phenyllithium which was condensed with camphor giving rise to [U-C-14-phenyl]borneol: (2) under bar. The latter, after conversion into its sodium salt, was reacted with dimethylaminoethyl chloride to give [C-14-Ar]Deramciclane, which was isolated as the fumarate salt. This 8 step synthesis from [C-14]BaCO3 gave an overall yield of 12 %. [1-C-14]Sodium acetate, through a standard 5 step literature procedure, was converted to N,N-dimethylaminoethyl-1-C-14 chloride (5) under bar which was condensed with the sodium derivative of 2-phenylborneol giving rise to [1-C-14-side chain]Deramciclane, again isolated as the fumarate. This 6 step synthesis from [C-14]BaCO3 gave an overall yield of 8 %. The specific radioactivities from the two syntheses were respectively 40 mCi/mmol and 21 mCi/mmol; chemical and radiochemical purities were better than 98 %.