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Improved synthesis of 13 C, 2 H 3 ‐ and 2 H 3 ‐salmeterol by Cs 2 CO 3 ‐mediated monoalkylation of a primary amine
Author(s) -
Molinski Tadeusz F.,
Stanley Scott D.
Publication year - 2002
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.595
Subject(s) - chemistry , alkylation , salmeterol , benzylamine , reagent , hexane , limiting , organic chemistry , amine gas treating , medicinal chemistry , catalysis , inhalation , medicine , mechanical engineering , engineering , anatomy
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.