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Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug

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Evangelos Aktoudianakis , Rui Jun Lin and Andrew P. Dicks

Department of Chemistry, University of Toronto, Ontario, Canada, M5S 3H6

J. Chem. Educ., 2006, 83 (12), p 1832

DOI: 10.1021/ed083p1832

Publication Date (Web): December 1, 2006

Section:

History, Education, and Documentation

Abstract

This article describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. The synthesis is straightforward and appropriate as part of a midlevel undergraduate organic laboratory. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter. This apprises students that atoms other than carbon can act as centers of chirality. The diastereotopic nature of protons adjacent to the sulfur stereocenter can be identified by ¹H NMR spectroscopy, and functional group changes monitored by IR spectroscopy. The nature of modafinil and its role in society as an anti-narcoleptic is a source of attraction and fascination among undergraduates.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Chirality / Optical Activity

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