912807-35-3

Usage

Uses

Used in Pharmaceutical Research:
(R)-3-N-tert-butoxycarbonylaminopiperidine is used as a building block for the synthesis of pharmaceuticals due to its versatile chemical properties and the protective role of the Boc group. This allows for the creation of various antiviral and anticancer drugs, contributing to the development of novel treatments for a range of diseases.
Used in Organic Chemistry:
In the field of organic chemistry, (R)-3-N-tert-butoxycarbonylaminopiperidine is used as an intermediate in the production of other chemicals. Its unique structure and the protective Boc group facilitate selective reactions, making it a valuable component in the synthesis of a wide array of chemical compounds.
Used in Chemical Reactions as a Reagent:
(R)-3-N-tert-butoxycarbonylaminopiperidine also serves as a reagent in chemical reactions, where its protective Boc group allows for selective reactions with other functional groups. This selective reactivity is crucial for achieving specific outcomes in complex chemical syntheses, further expanding the compound's utility in research and development.

Upstream product

• 885949-15-5 (R)-(-)-3-piperidinecarboxylic acid hydrochloride 
• 540-88-5 acetic acid tert-butyl ester 
• 498-95-3 (R)-nipecotic acid 
• 160706-62-7 (R)-1-((benzyloxy)carbonyl)piperidine-3-carboxylic acid 
• 912807-34-2 (R)-piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-tert-butyl ester 

Downstream Products

• 668270-12-0 Linagliptin 
• 912807-36-4 (R)-1-[(1R,2R,3S)-3-{(R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy}-2-(4-fluorophenyl)cyclopentylmethyl]piperidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Challenges in the Development of a Thiol-Based Broad-Spectrum Inhibitor for Metallo-β-Lactamases

Pathogens, expressing metallo-β-lactamases (MBLs), become resistant against most β-lactam antibiotics. Besides the dragging search for new antibiotics, development of MBL inhibitors would be an alternative weapon against resistant bacterial pathogens. Inhibition of resistance enzymes could restore the antibacterial activity of β-lactams. Various approaches to MBL inhibitors are described; among others, the promising motif of a zinc coordinating thiol moiety is very popular. Nevertheless, since the first report of a thiol-based MBL inhibitor (thiomandelic acid) in 2001, no steps in development of thiol based MBL inhibitors were reported that go beyond clinical isolate testing. In this study, we report on the synthesis and biochemical characterization of thiol-based MBL inhibitors and highlight the challenges behind the development of thiol-based compounds, which exhibit good in vitro activity toward a broad spectrum of MBLs, selectivity against human off-targets, and reasonable activity against clinical isolates.

Stereoselective preparation of a cyclopentane-based NK1 receptor antagonist bearing an unsymmetrically substituted sec-sec ether

A highly efficient synthesis of the potent and selective NK-1 receptor antagonist 1 is described. The key transformation involved the etherification reaction between cyclopentanol 12 and chiral imidate 30 which was catalyzed by HBF4 to initially give ether 14 as a 17:1 mixture of diastereomers and in 75% combined yield. The diastereoselectivity was upgraded to 109:1 by crystallization of the triethylamine solvate 44 which was isolated in 54% yield from 12. Mechanistic studies confirmed that the etherification reaction proceeds through an unprecedented SN2 reaction pathway under typical S N1 reaction conditions.