A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid |
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| Institution: | 1. European Commission, Directorate General-Joint Research Centre, Institute for Reference Materials and Measurements (IRMM), Retieseweg 111, Geel 2440, Belgium;2. European Chemicals Agency, Annankatu 18, Helsinki 00121, Finland;1. Department of Orthopaedics and Traumatology, Nanfang Hospital, Southern Medical University, 1838 North Guangzhou Avenue, Guangzhou City, Guangdong Province 510515, People''s Republic of China;2. Department of Orthopaedics, Xiangyang Central Hospital, Xiangyang City, Hubei Province 441021, People''s Republic of China |
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| Abstract: | (S)-3-Hydroxytetradecanoic acid 1 has been synthesized in an overall yield of 27% from (S)-epichlorohydrin 2 as follows: (1) regio and chemoselective epoxide opening of 2 with a Grignard reagent under the catalysis by Cu(I) followed by consecutive epoxide formation; (2) regioselective epoxide opening of (S)-1,2-epoxytridecane 4 with cyanide anion under pH controlled conditions followed by consecutive nitrile hydrolysis with alkaline H2O2 gave crude 1; (3) its purification via the N,N-dicyclohexylammonium salt 6. The method thus devised is practical and scalable for the industrial production of 1. |
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