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

Add time:09/08/2019    Source:sciencedirect.com

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 cinnamyl alcohol. A Curtius rearrangement and subsequent deprotection provides 1 in high yield and excellent enantiomeric excess.

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