On December 15, 2012, Isherwood, Matthew L.; Guzzo, Peter R.; Henderson, Alan J.; Hsia, Ming Min; Kaur, Jagjit; Nacro, Kassoum; Narreddula, Venkateswara R.; Panduga, Shailaja; Pathak, Rashmi; Shimpukade, Bharat; Tan, Valentina; Xiang, Kai; Qiang, Zhu; Ghosh, Animesh published an article.Quality Control of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate The title of the article was An efficient synthesis of (7S,10R)-2-bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole: application in the preparation and structural confirmation of a potent 5-HT6 antagonist. And the article contained the following:
(7S,10R)-5-Methyl-2-((3-(trifluoromethyl)phenyl)sulfonyl)-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole I is a potent 5-HT6 antagonist (h5-HT6Ki = 1.5 nM) which is derived from an epiminocyclohept[b]indole scaffold. In order to synthesize I on a multi-gram scale to support advanced biol. testing, an efficient chiral resolution of the intermediate tert-Bu 2-bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-11-carboxylate II was developed. After derivatizing II with (1R)-(-)-menthyl chloroformate it was found that a single diastereomer III could be isolated by selective precipitation from n-hexane. The absolute stereochem. of III was determined by X-ray crystallog. and the structure was confirmed as (7S,10R)-tert-Bu 2-bromo-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-11-carboxylate. Removal of the chiral auxiliary under basic conditions afforded intermediate II in >99% enantiomeric purity and with 80% yield based on recovery from the racemic compound II. Intermediate enantiomer II was used successfully to synthesize 5-HT6 antagonist I on a multi-gram scale. The experimental process involved the reaction of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate(cas: 14602-86-9).Quality Control of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate
The Article related to methyltrifluoromethylphenylsulfonylhexahydroepiminocycloheptaindole preparation chem resolution, substitution hydrolysis, butylbromohexahydroepiminocycloheptaindolecarboxylate menthyl chloroformate separation hydrolysis methylation and other aspects.Quality Control of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate
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