An efficient synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin) via quinine-mediated desymmetrization of cyclic anhydride |
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| Institution: | 1. Department of Organic Chemistry and Biochemistry, Rudjer Bošković Institute, PO Box 180, 10002 Zagreb, Croatia;2. PLIVA Research and Development Ltd, Prilaz Baruna Filipovića 29, 10000 Zagreb, Croatia |
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| Abstract: | 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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