![\"RRR](\"http:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/4\/4a\/RRRsynthesis.png\/400px-RRRsynthesis.png\")
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In one of its steps the\u00a0racemic<\/a>\u00a0alcohol<\/a>\u00a01<\/strong>\u00a0is dissolved in a mixture of\u00a0toluene<\/a>\u00a0and\u00a0methanol<\/a>\u00a0to which solution is added optically active (S)-mandelic acid<\/a>\u00a03<\/strong>. The alcohol (S)-enantiomer forms an insoluble\u00a0diastereomeric<\/a>\u00a0salt with the mandelic acid and can be filtered from the solution. Simple deprotonation with\u00a0sodium hydroxide<\/a>\u00a0liberates free (S)-alcohol. In the meanwhile the (R)-alcohol remains in solution unaffected and is recycled back to the racemic mixture by\u00a0epimerization<\/a>\u00a0with\u00a0hydrochloric acid<\/a>\u00a0in toluene. This process is known asRRR synthesis<\/strong>\u00a0in which the R’s stand for\u00a0Resolution-Racemization-Recycle<\/strong>. ref 1,2,3<\/p>\n This is a \u00a0modern-day method of chiral resolution \u00a0used in the\u00a0organic synthesis<\/a>\u00a0of the drug\u00a0Duloxetine<\/a>: ref\u00a04<\/span><\/p>\n (S<\/em>)-3-(N<\/em>-methylamino)-1-(2-thienyl)propan-1-ol (1<\/strong>) of 100% ee, an alleged penultimate precursor to duloxetine<\/p>\n In one of its steps the\u00a0racemic\u00a0alcohol\u00a01\u00a0is dissolved in a mixture of\u00a0toluene\u00a0and\u00a0methanol\u00a0to which solution is added optically active (S)-mandelic acid\u00a03. The alcohol (S)-enantiomer forms an insoluble\u00a0diastereomeric\u00a0salt with the mandelic acid and can be filtered from the solution. Simple deprotonation with\u00a0sodium hydroxide\u00a0liberates free (S)-alcohol. In the meanwhile the (R)-alcohol remains in solution unaffected and is recycled back… Continue reading Resolution-Racemization-Recycle.<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[143],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/86"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=86"}],"version-history":[{"count":3,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/86\/revisions"}],"predecessor-version":[{"id":88,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/86\/revisions\/88"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=86"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=86"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=86"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}References<\/h2>\n
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![\"Abstract](\"http:\/\/pubs.acs.org\/appl\/literatum\/publisher\/achs\/journals\/content\/oprdfk\/2006\/oprdfk.2006.10.issue-5\/op060118l\/production\/images\/medium\/op060118ln00001.gif\")
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