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Synthesis of Deramciclane labelled with radiocarbon in various positions
Author(s) -
Szammer J.,
SimonTrompler E.,
Máté J.,
Abermann M.,
Ürmös I.,
Klebovich I.
Publication year - 1997
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199712)39:12<1011::aid-jlcr49>3.0.co;2-z
Subject(s) - chemistry , yield (engineering) , bromobenzene , sodium carbonate , phenyllithium , sodium , camphor , barium carbonate , chloride , derivative (finance) , nuclear chemistry , organic chemistry , medicinal chemistry , raw material , catalysis , materials science , economics , financial economics , metallurgy
[U‐ 14 C]Bromobenzene, prepared from [ 14 C]barium carbonate according to literature procedures, was transformed (Li/diethylether) into [ 14 C]phenyllithium which was condensed with camphor giving rise to [U‐ 14 C‐phenyl]borneol: 2. The latter, after conversion into its sodium salt, was reacted with dimethylaminoethyl chloride to give [ 14 C‐Ar]Deramciclane, which was isolated as the fumarate salt. This 8 step synthesis from [ 14 C]BaCO 3 gave an overall yield of 12%. [1‐ 14 C]Sodium acetate, through a standard 5 step literature procedure, was converted to N,N‐dimethylaminoethyl‐1‐ 14 C chloride 5 which was condensed with the sodium derivative of 2‐phenylborneol giving rise to [1‐ 14 C‐side chain]Deramciclane, again isolated as the fumarate. This 6 step synthesis from [ 14 C]BaCO 3 gave 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%. © 1997 John Wiley & Sons, Ltd.