An efficient synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin) via quinine-mediated desymmetrization of cyclic anhydride

作者：Hamersak Zdenko^*; Stipetic Irena; Avdagic Amir

来源：Tetrahedron: Asymmetry , 2007, 18(12): 1481-1485.

DOI：10.1016/j.tetasy.2007.06.014

A highly enantioselective synthesis of (S)-3-aminomethyl-5-methylhexanoic acid 1 (Pregabalin) is reported. The key step of the synthesis is a quinine-mediated ring opening of 3-isobutylglutaric anhydride with cinnarryl alcohol. A Curtius rearrangement and subsequent deprotection provides 1 in high yield and excellent enantiomeric excess.

• 出版日期2007-7-4