- A new asymmetric synthetic route to substituted piperidines
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An asymmetric synthesis of substituted piperidines has been described. β-Cyclodextrin- or oxazaborolidine-catalyzed asymmetric reduction of α-azido aryl ketones to the corresponding alcohols has been employed as the key step along with ring closing metathesis and selective dihydroxylation.
- Reddy, M. Somi,Narender,Rao, K. Rama
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- Method for industrially producing (S)-3-(4-bromophenyl) piperidine
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The invention belongs to the field of chemical medicine synthesis, and provides a method for industrially producing (S)-3-(4-bromophenyl) piperidine. The method comprises the following steps: by taking (S)-1-tert-butyloxycarbonyl-3-hydroxypiperidine as an initial raw material, removing tert-butyloxycarbonyl protecting groups to obtain (S)-3-hydroxypiperidine hydrochloride A; condensing the intermediate A and thionyl chloride to generate a five-membered ring sulfinate intermediate B; oxidizing the intermediate B to generate a five-membered ring sulfonate C; carrying out nucleophilic substitution reaction on the compound C and aryl anions, and meanwhile, carrying out configuration inversion to generate the target product (S)-3-(4-bromophenyl) piperidine. According to the whole process, high-pressure hydrogenation, diazotization and other operations are not used, and no chiral resolution reagent is used, so that the total cost is lower, the operation is simple and convenient, higher chiral purity can be maintained, and the method is suitable for industrial large-scale production.
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Paragraph 0060; 0061; 0065; 0066; 0070; 0071
(2020/02/14)
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