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Improved synthesis of 13C,2H3- and 2H3-salmeterol by Cs2CO3-mediated monoalkylation of a primary amine

✍ Scribed by Tadeusz F. Molinski; Scott D. Stanley

Publisher: John Wiley and Sons
Year: 2002
Tongue: French
Weight: 153 KB
Volume: 45
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.595

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✦ Synopsis

Abstract

An abbreviated synthesis of isotopically labelled salmeterol has been achieved. The key improvement utilizes a highly selective Cs~2~CO~3~‐mediated one‐pot alkylation of benzylamine by 6‐bromo‐1‐(4′‐phenylbutoxy)hexane to prepare the limiting reagent, 6‐N‐benzylamino‐1‐(4′‐phenylbutoxy)hexane without overalkylation. The method was applied to synthesis of the title compounds in >97 at% isotopic purity. Copyright © 2002 John Wiley & Sons, Ltd.

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