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Synthesis of deramciclane* labeled with tritium in various positions

✍ Scribed by János Szammer; Edit Simon-Trompler; Zoltán Banka; József Szúnyog; Imre Klebovich

Book ID
102375976
Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
108 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis

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.

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