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CHEMDOODLE HOW TO DRAW BRIDGED BICYCLI PLUS
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The process for the synthesis of (2S,3aR,7aS)-octahydroindole-2-carboxylic acid is described in the US Patent 6,559,318 and reported in the scheme VI.ĭr. Octahydrindole-2-carbonitrile is hydrolyzed to give octahydroindole-2-carboxylic acid of formula III a. This product is converted into a mixture of octahydroindole-2-carbonitrile of formula XXVIII a and XXVIII b. The product of formula XXVI, in reaction with methane sulphonyl chloride and benzoyl chloride give a product of formula XXVII. This product is subject to the Hoffmann reaction, followed by reaction with formaldehyde and potassium cyanide to give cyclohexyl amine derivative of formula XXVI. This product is treated with ammonia to give cyclohexane carboxamide of formula XXV.
The product of formula XXII is reacted with pyrrolidine to yield a product of formula XXIII which is converted to hexahydroisobenzofuranone of formula XXII a. Dimethyl-1,2-cyclohexane dicarboxylate of formula XX is enzymatically resolved to give the monomethyl ester of 1,2-cyclohexane dicarboxylic acid of formula XXI, which is converted into hexahydroisobenzofuranone of formula XXII.
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