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Article Abstract
A concise, recyclable, and efficient process is presented for the preparation of ()-ketamine (esketamine, ()-) via classic resolution combined with the recycling of the undesired isomer. With commercially available ketone as the starting material, this procedure features three steps including (1) an unique hydroxylation-ring expansion rearrangement, (2) mild amination via methanesulfonate, and (3) chiral separation using -(+)-tartaric acid. The three simple steps are all performed in mild conditions and ()- tartrate is obtained in 99.5% ee without recrystallization. Subsequently, racemization of the unwanted ()- remained in resolution mother liquor was performed in the presence of a Lewis acid in quantitative yield with >99.0% chemical purity. This original and economical process afforded esketamine in 67.4% (28.9% without racemization) overall yield with two times recycling of the mother liquor without column purification. In addition, this procedure can also be applied to the preparation of ()-norketamine, which is a safer potential antidepressant.
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