Synthesis of deramciclane labeled with tritium in various positions

[(1R)‐endo]‐(+)‐3‐bromocamphor was dehalogenated with tritium gas to [3‐3H]camphor and via [3‐3H]phenylborneol converted to [3‐3H]deramciclane isolated as the fumarate salt (specific activity 51.8 GBq/mmol). This three step synthesis from [3‐3H]camphor gave an overall yield of 22%. Benzyloxy‐acetic acid methyl ester was reduced with sodium‐borotritide to 2‐benzyloxy‐ethanol‐[1‐3H], and through a four step procedure was converted to 2‐dimethylaminoethyl‐[2‐3H] chloride. The latter was condensed with the sodium derivative of 2‐phenylborneol giving rise to [2‐dimethylamino‐[2‐3H]ethoxy]deramciclane isolated as the fumarate (specific activity 8.177 GBq/mmol). This six step synthesis from [3H]NaBH4 gave an overall yield of 6%. Copyright © 2005 John Wiley & Sons, Ltd.