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Synthesis of deramciclane * labeled with tritium in various positions
Author(s) -
Szammer János,
SimonTrompler Edit,
Banka Zoltán,
Szúnyog József,
Klebovich Imre
Publication year - 2005
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/jlcr.964
Subject(s) - chemistry , yield (engineering) , tritium , camphor , acetic acid , sodium , tritium illumination , sodium salt , nuclear chemistry , derivative (finance) , ethanol , medicinal chemistry , specific activity , radiochemistry , organic chemistry , inorganic chemistry , enzyme , physics , materials science , nuclear physics , financial economics , economics , metallurgy
Abstract [(1 R )‐ endo ]‐(+)‐3‐bromocamphor was dehalogenated with tritium gas to [3‐ 3 H]camphor and via [3‐ 3 H]phenylborneol converted to [3‐ 3 H]deramciclane isolated as the fumarate salt (specific activity 51.8 GBq/mmol). This three step synthesis from [3‐ 3 H]camphor gave an overall yield of 22%. Benzyloxy‐acetic acid methyl ester was reduced with sodium‐borotritide to 2‐benzyloxy‐ethanol‐[1‐ 3 H], and through a four step procedure was converted to 2‐dimethylaminoethyl‐[2‐ 3 H] chloride. The latter was condensed with the sodium derivative of 2‐phenylborneol giving rise to [2‐dimethylamino‐[2‐ 3 H]ethoxy]deramciclane isolated as the fumarate (specific activity 8.177 GBq/mmol). This six step synthesis from [ 3 H]NaBH 4 gave an overall yield of 6%. Copyright © 2005 John Wiley & Sons, Ltd.