Improved synthesis of  13 C, 2 H 3 ‐ and  2 H 3 ‐salmeterol by Cs 2 CO 3 ‐mediated monoalkylation of a primary amine | Zendy

Molinski Tadeusz F. | Zendy; Stanley Scott D. | Zendy

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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.

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