Issue 21, 1996
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites

James E. Jeffery,   Frank Kerrigan,   Thomas K. Miller,   Graham J. Smith  and  Gerald B. Tometzki  

Abstract

Synthetic routes to N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine (sibutramine) 1 and its demethylated and hydroxylated human metabolites N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N-methylamine 2, 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine 3, 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-1-ol 4 and c-3-(1-amino-3-methylbutyl)-3-(4-chlorophenyl)cyclobutan-r-1-ol 5a are described. Key steps are tandem Grignard–reduction reactions on 1-(4-chlorophenyl)cyclobutanecarbonitrile 7 and its 3-(tetrahydropyran-2-yloxy)-substituted analogue 14 and a convenient one-pot conversion of 4-chlorophenylacetonitrile 6 into the 3-hydroxycyclobutanecarbonitrile 13.

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Article information

DOI
https://doi.org/10.1039/P19960002583
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1996, 2583-2589

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Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites

J. E. Jeffery, F. Kerrigan, T. K. Miller, G. J. Smith and G. B. Tometzki, J. Chem. Soc., Perkin Trans. 1, 1996, 2583 DOI: 10.1039/P19960002583

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