Aldrich ChemFiles 2007, 7.8, 7.

Aldrich ChemFiles 2007, 7.8, 7.

Piperidines have become increasingly popular building blocks in a vast array of synthetic protocols. 1-Boc-2-(aminomethyl)piperidine has been used in a post-Ugi carbonylation/intramolecular amidation approach to a series of eight-membered macrolactams with multiple points of diversity (Scheme 1). 1 On the other hand, the unprotected analogue has been employed in the synthesis of melanocortin 4 receptor antagonists (Scheme 2). These antagonists are potentially useful in the therapeutic treatment of involuntary weight loss. 2

Scheme 1(687154)

Scheme 2(656518)

Fluorinated piperidines are also showing increased interest in medicinal chemistry. Both 3- and 4-fluoropiperidine were used in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors (Scheme 3). The 3-fluoro analogue in particular demonstrated improved selectivity, without sacrificing potency. 3

Scheme 3(680168)(665606)

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  1. Vasudevan, A.; Verzal, M. K. Tetrahedron Lett. 2005, 46, 1697.
  2. Marsilje, T. H. et al. Bioorg. Med. Chem. Lett. 2004, 14, 3721.
  3. Senten, K. et al. J. Med. Chem. 2004, 47, 2906.

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