Unusual p-Toluene Sulfonic Acid-Catalyzed Carbon-Carbon Bond Formation

Attempts to synthesize the antidepressant drug atomoxetine directly by p-TSA-catalyzed reaction between o-cresol and N-methyl-3-phenyl-3-hydroxypropyl amine in toluene at reflux temperature surprisingly resulted in the formation of ortho-substituted phenol derivative. The structure is unambiguously...

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Bibliographic Details
Published in:Synthetic communications 2005-07, Vol.35 (13), p.1765-1768
Main Authors: Govindan, Shanmugam, Maddipatla, Madhavi, Podichetty, Anil Kumar, Macharla, Prabhakahr, Nalivela, Venu, Sundaram, Venkataraman, Mathad, Vijayavitthal T., Ghanta, Mahesh Reddy, Yalavarti, Ravindra Kumar
Format: Article
Language:English
Subjects:
antidepressant drug
Aromatic substitution
atomoxetine
carbon-carbon bond formation
p-toluenesulfonic acid
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Summary:Attempts to synthesize the antidepressant drug atomoxetine directly by p-TSA-catalyzed reaction between o-cresol and N-methyl-3-phenyl-3-hydroxypropyl amine in toluene at reflux temperature surprisingly resulted in the formation of ortho-substituted phenol derivative. The structure is unambiguously confirmed by single crystal X-ray.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-200063935