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The synthesis and separation of [3-2H]tropine and [3-2H]pseudotropine (ψ-tropine)

✍ Scribed by Barbara A. Bartholomew; Michael J. Smith; Paul J. Darcy; Peter W. Trudgill; David J. Hopper

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
246 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Tropinone was reduced using sodium borodeuteride to give a mixture of the epimers [3‐^2^H] tropine and [3‐^2^H]pseudotropine with the latter compound predominating and constituting about 70% of the mixture. Crystallisation of the product from diethyl ether gave crystals of pure [3‐^2^H]pseudotropine and a supernatant solution containing a mixture of the epimers. Acetylation of this mixture using acetyl chloride preferentially acetylated the pseudotropine and the acetylated products were separated from the tropine by flash chromatography to leave a sample of pure [3‐^2^H]tropine.

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