Journal
TETRAHEDRON LETTERS
Volume 51, Issue 18, Pages 2403-2405Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.02.089
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Funding
- NIH [R37 DE 014193, UL1 RR025741, U54 CA119341]
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Direct acetonide protection of the catechol of dopamine has proven to be problematic due to the formation of Pictet-Spengler isoquinolines. Here we report an efficient method for acetonide protection of dopamine, allowing the preparation of a dopamine prodrug without complications from the Pictet-Spengler reaction. Acetonide-protected dopamine was first synthesized by pre-protecting the amino group with phthaloyl followed by refluxing with 2,2-dimethoxypropane in the presence of MOH. Further work demonstrated that Fmoc and trifluoroacetyl were also suitable N-protective groups, while Boc-protected dopamine gave an isoquinoline product. Acetonide-protected dopamine was coupled to DHA (all cis-4,7,10,13,16,19-docosahexaenoic acid) to produce the N-DHA-dopamine prodrug with high purity. (C) 2010 Elsevier Ltd. All rights reserved.
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