A route for the synthesis of (S,S)-7-amino-5-methyl-5H-dibenzo[b,d]azepin-6(7H)-one hydrochloride is disclosed. The synthesis includes a Friedel–Crafts alkylation to form the seven-membered ring and a highly efficient classical resolution. Additional studies on the enantiopure material showed the amine to be highly resistant to racemization, which led us to investigate the unexpected stability. We propose that the inherent axial chirality contained in the dibenzazepinone works to produce an interesting chirality transfer mechanism, which accounts for the observed robustness of the stereocenter. This previously unrecognized stereochemical element exists within this specific class of molecules, and they should be drawn in a manner which displays the axial chirality.

中文翻译：

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对映纯氨基二苯并ze庚酮的合成和轴向手性

（S，S）-7-氨基-5-甲基-5 H-二苯并[ b，d ] azepin-6（7 H公开了一种盐酸盐。合成过程包括Friedel-Crafts烷基化反应以形成七元环和高效的经典拆分方法。对对映纯材料的其他研究表明，胺对消旋具有很高的抵抗力，这使我们研究了意外的稳定性。我们建议，二苯并ze庚酮中固有的轴向手性可产生有趣的手性转移机制，这说明了所观察到的立体中心的鲁棒性。这种先前无法识别的立体化学元素存在于这种特定的分子类别中，应以显示轴向手性的方式进行绘制。