An efficient stereoselective synthesis of six stereoisomers of 3, 4-diaminocyclohexane carboxamide as key intermediates for the synthesis of factor Xa inhibitors
2017
Wang, Xin | Ma, Mingliang | Reddy, A Gopi Krishna | Hu, Wenhao
An efficient stereoselective route for the preparation of six stereoisomers of tert-butyl ((1R, 2S, 5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate 1 starting from simple 3-cyclohexene-1-carboxylic acid has been described. Stereochemistry of the title compounds was controlled at C2 center by Mitsunobu reaction and at C5 via a base-catalyzed epimerization. Only a limited usage of column chromatography has provided a direct and scalable route for the six stereoisomers.
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