Taira Kimino, I. Fujii
2013
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X-ray Structure Analysis Online
Abstract
The production of chiral compounds has great importance in the pharmaceutical industry, and diastereomer salt separation has still been widely applied in the process. One of the title compounds, (1S,2R)-2-(benzamido)cyclohexanecarboxylic acid, BACO (I), was used as such a chiral resolving agent,1 but it was originally synthesized in stereochemical studies,2 and its ciscyclicamino acid is used as an intermediate for an analog of GABA.3,4 It was considered that (I) and its reduction product, (1S,2R)-2-(benzylamino)cyclohexylmethanol, BACH (II),5 recognized the amine/amino-alcohol and carboxy groups in diastereomer salts, respectively, but the structures have not been cleared. In this study, the crystal structures of (I) and (II) were determined and correlated with their chemical properties. The compounds were purchased from Tokyo Chemical Industry (TCI). Rod-shaped crystals of (I) and plate-like crystals of (II) were obtained from ethanol and chloroform mixture solutions. Crystal and experimental data are given in Table 1. The crystal structures were solved by direct methods (SHELXS-97),6 and refined by full-matrix least squares. The absolute configurations were chosen from the relationship1 to the optical rotations, [a]D = +36 and –24 ̊ (c = 1, in methanol) of X-ray Structure Analysis Online