Synthesis of deramciclane * labeled with tritium in various positions

[(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.