A short enantioselective synthesis of N-Boc-(2R,3R)-3-methyl-3-hydroxypipecolic acid from geraniol |
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Authors: | Noe Mark C Hawkins Joel M Snow Sheri L Wolf-Gouveia Lilli |
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Affiliation: | Pfizer Global Research and Development, Eastern Point Road, Groton, Connecticut 06340, USA. mark.c.noe@pfizer.com |
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Abstract: | The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring. |
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