Preparation of (<i>R</i>)‐3‐aminopiperidine by resolution with optically active cyclic phosphoric acids

Sun, Yujuan; Hu, Beibei; Jing, Yongshuai; Wu, Jialiang; Zhou, Maochao; Chen, Meng; Hao, Feifei; Zhang, Chen; Sun, Fei

doi:10.1002/chir.23312

Cited by 2 publications

(1 citation statement)

References 6 publications

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“…This development was accompanied by an intensive search for procedures for the resolution of racemic derivatives of 2 , resulting in a steadily increasing number of powerful variants . An alternative approach relies on derivatives of nipecotic acid ( 3 ), which are subsequently converted to 2 by a Curtius-, Hofmann-, or Lossen-type rearrangement .…”

Section: Introductionmentioning

confidence: 99%

Preparation of Enantiopure 3-Aminopiperidine and 3-Aminoazepane Derivatives from Ornithine and Lysine. Consecutive Syntheses of Pharmacologically Active Analogs, Such as Besifloxacin

Schiffers

Frings

Kübber

et al. 2022

Org. Process Res. Dev.

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In recent years, 3-aminopiperidine and 3-aminoazepane have been identified as important pharmacophores that led to the development of drugs having several billion dollar global revenues. Although the number of protocols for the resolution of suitable racemic derivatives is steadily increasing, there is an ongoing demand for new synthetic methods to prepare enantiomerically pure analogs from readily available starting materials. Herein, we report the cyclization of methyl esters derived from natural ornithine and lysine as well as their enantiomeric counterparts. Lactam synthesis was regularly performed on a lab scale of up to 150 mmol per batch. Protection and subsequent reduction to enantiopure 3-(tritylamino)piperidine and 3-(tritylamino)azepane allowed the selective derivatization of the heterocyclic nitrogen. Deprotection gave access to a set of building blocks that were applied to the synthesis of eight molecules reported to be pharmacologically active in drug research. For example, besifloxacin was prepared in only a few steps starting from D-lysine.

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Section: Introductionmentioning

confidence: 99%

Preparation of Enantiopure 3-Aminopiperidine and 3-Aminoazepane Derivatives from Ornithine and Lysine. Consecutive Syntheses of Pharmacologically Active Analogs, Such as Besifloxacin

Schiffers

Frings

Kübber

et al. 2022

Org. Process Res. Dev.

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Quinquevalent phosphorus acids

Bałczewski,

Owsianik

2024

Organophosphorus Chemistry

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This chapter shows, as in previous years, the most important achievements of the 2021 year in the area of organo-phosphorus compounds containing: three P–O bonds (Section 2: phosphoric acids and their derivatives), two P–O and one P–C bonds (Section 3: phosphonic acids and their derivatives) as well as one P–O and two P–C bonds (Section 4: phosphinic acids and their derivatives), in addition to the phosphoryl group P═O, present in all three groups of compounds. Each of the main sections covers “synthesis and reactions” including pure synthesis without applications, “synthesis and biological applications” and “synthesis and miscellaneous applications” including synthesis directed towards non-biological applications. At the end of each subsection, the corresponding achievements are shown for hetero-analogues in which phosphorus–oxygen bonds have been replaced by phosphorus–heteroatom P–X and/or P═Y bonds (X, Y = N, S or Se). The subsection on quinquevalent phosphorus acids and their derivatives as catalysts has been placed, as usual, at the end of the entire chapter, after a review of all three main groups of compounds. As in previous years, the area devoted to phosphoric and phosphonic acids and their derivatives dominated over a smaller section of phosphinic acids and their derivatives, and literature references for these sections remained at a ratio of 4 : 12 : 1. A dynamic, five-fold increase in the number of works, in the subject of chiral phosphoric acids as catalysts, has been recorded in this year.

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Preparation of (R)‐3‐aminopiperidine by resolution with optically active cyclic phosphoric acids

Cited by 2 publications

References 6 publications

Preparation of Enantiopure 3-Aminopiperidine and 3-Aminoazepane Derivatives from Ornithine and Lysine. Consecutive Syntheses of Pharmacologically Active Analogs, Such as Besifloxacin

Preparation of Enantiopure 3-Aminopiperidine and 3-Aminoazepane Derivatives from Ornithine and Lysine. Consecutive Syntheses of Pharmacologically Active Analogs, Such as Besifloxacin

Quinquevalent phosphorus acids

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