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The preparation of deuterium- and tritium-labeled pirbuterol hydrochloride

✍ Scribed by Hugh M. McIlhenny

Publisher
John Wiley and Sons
Year
1976
Tongue
French
Weight
449 KB
Volume
12
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A mild exchange labeling procedure utilizing O‐deuterated or O‐tritiated t‐butanol with sodium catalysis afforded isotope exchange in the α‐hydrogen position of the amide N‐t‐butyl‐2‐(5‐benzyloxy‐6‐hydroxymethyl‐2‐pyridyl)‐2‐hydroxy‐acetamide, thereby extending the utility of this approach with ketones to poor enolizers that are base labile. Complete label retention accompanied the subsequent steps of reduction and debenzylation to 2‐hydroxymethyl‐3‐hydroxy‐6(l‐hydroxy‐2‐t‐butylaminoethyl)‐pyridine dihydrochloride (pirbuterol hydrochloride)‐^2^H or ‐^3^H, in 15‐18% overall yield at the 4 mmole level. Deuterium incorporation was estimated to be 39%; a specific activity of 206 μc/mg was achieved by radiolabeling. A radiochemical and chemical purity of > 99.5% was established. Tritium label stability was demonstrated in aqueous media at acidic, neutral and basic pH.

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