Development of an Asymmetric Hydrogenation Route to (S)-N-Boc-2,6-dimethyltyrosine

An improved, simpler and potentially more economical route to (S)-N-Boc-2,6-dimethyltyrosine 1, based on a previously published route, is presented. Key modifications were to prepare the dehydroaminoacid hydrogenation substrate 6 in a one-pot process directly from serine methyl ester and 4-iodo-3,5-...

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Published inOrganic process research & development Vol. 15; no. 5; pp. 1124 - 1129
Main Authors Praquin, Céline F. B, de Koning, Pieter D, Peach, Philip J, Howard, Roger M, Spencer, Sarah L
Format Journal Article
LanguageEnglish
Published American Chemical Society 16.09.2011
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Summary:An improved, simpler and potentially more economical route to (S)-N-Boc-2,6-dimethyltyrosine 1, based on a previously published route, is presented. Key modifications were to prepare the dehydroaminoacid hydrogenation substrate 6 in a one-pot process directly from serine methyl ester and 4-iodo-3,5-dimethylphenyl acetate 4 and to identify a significantly more active asymmetric hydrogenation catalyst that allowed a 5-fold reduction in catalyst loading.
ISSN:1083-6160
1520-586X
DOI:10.1021/op200065p