Abstract
Fentanyl of a potent anilidopiperidine analgesic has been synthesized from a simple phenyle-thylamine by four step sequence. The key part of this synthesis involves an efficient construction of phenylethylpiperidone skeleton via aminomethano desilyation-cyclization followed by Swern oxidation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References Cited
Borne, R. F., Fifer, E. K. and Waters, I. W., Conformationally restrained fentanyl analogues., 2. Synthesis and analgesic evaluation of perhydro-1,6-naphthyri-din-2-ones.,J. Med. Chem., 27, 1271–1275 (1984) and references cited therein.
Janssen, P. J. A. and Van der Eycken, A. M.,Drugs affecting the central nervous system, Burget, A. Ed., Marcel Dekker, New York, 1968, pp 51–54.
Grieco, P. A. and Fobare, W. F., Intramolecular variants of aminomethano desilylation: Reactions ofin situ generated immonium Ions with allylsilanes.,Tetrahedron Lett., 27, 5067–5070 (1986).
Larsen, S. D., Grieco, P. A. and Fobare, W. F., Reactions of allylsilanes with simple iminium salts in water: A facile route to piperidines via an aminomethano desilylation-cyclization process.,J. Am. Chem. Soc., 108, 3512–3513 (1986).
Lednicer, D. and Mitscher, L. A., The organic chemistry of drug synthesis, John Wiley & Sons, New York, 1, pp 286–311 (1977).
Omura, K. and Swern, D., Oxidation of alcohols by “activated” dimethyl sulfoxide. A preparative steric and mechanistic study.,Tetrahedron, 34 1651–1660 (1978).
Suh, Y.-G., Shin, D.-Y., Cho, K.-H. and Ryu, J.-S., Concise and versatile synthesis ofN-arylalkylpiperidine as potential intermediates for 4-anilidopiperidine analgesics.Heterocycles, in press.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Suh, YG., Cho, KH. & Shin, DY. Total synthesis of fentanyl. Arch. Pharm. Res. 21, 70–72 (1998). https://doi.org/10.1007/BF03216756
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF03216756