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The synthesis and separation of [3‐ 2 H]tropine and [3‐ 2 H]pseudotropine (ψ‐tropine)
Author(s) -
Bartholomew Barbara A.,
Smith Michael J.,
Darcy Paul J.,
Trudgill Peter W.,
Hopper David J.
Publication year - 1994
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.2580340112
Subject(s) - chemistry , epimer , acetylation , stereochemistry , chromatography , biochemistry , gene
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.