A Green, Enantioselective Synthesis of Warfarin for the Undergraduate Organic Laboratory
The enantioselective synthesis of drugs is of fundamental importance in the pharmaceutical industry. In this experiment, students synthesize either enantiomer of warfarin, a widely used anticoagulant, in a single step from inexpensive starting materials. Stereoselectivity is induced by a commercial organocatalyst, (R,R)- or (S,S)-1,2-diphenylethylenediamine. The environmentally friendly microscale reaction is performed at ambient temperature, and the product can be purified by recrystallization or column chromatography. Product characterization includes thin-layer chromatography, NMR spectroscopy, and polarimetry.
© 2010 The American Chemical Society and Division of Chemical Education, Inc.
“A green, enantioselective synthesis of warfarin for the undergraduate organic laboratory,” Wong, T.C.; Sultana, C.M.; Vosburg, D.A. J. Chem. Educ. 2010, 87, 194-195. DOI: 10.1021/ed800040m