150197-75-4 Usage
Description
(2S,5S)-5-hydroxy-2-methylpiperidine is a heterocyclic amine with the molecular formula C6H13NO. It features a six-membered ring structure composed of five carbon atoms and one nitrogen atom, with specific stereochemistry at the 2nd and 5th positions, both in the S (sinister) configuration. The molecule is further characterized by a hydroxy group at the 5th position and a methyl group at the 2nd position, which confer unique properties and reactivity to the compound. This piperidine derivative holds potential in the realms of organic synthesis and medicinal chemistry due to its distinctive structural attributes.
Uses
Used in Organic Synthesis:
(2S,5S)-5-hydroxy-2-methylpiperidine serves as a valuable intermediate in organic synthesis, particularly for the creation of complex organic molecules. Its unique structure allows for selective reactions and functional group manipulations, making it a versatile building block for the development of novel compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S,5S)-5-hydroxy-2-methylpiperidine is utilized as a key component in the design and synthesis of pharmaceutical agents. Its specific stereochemistry and functional groups can be leveraged to create molecules with targeted biological activities, potentially leading to the discovery of new drugs with improved efficacy and selectivity.
Used in Pharmaceutical Development:
(2S,5S)-5-hydroxy-2-methylpiperidine is employed in pharmaceutical development as a precursor for the synthesis of various drug candidates. Its unique structural features can be exploited to enhance the pharmacokinetic and pharmacodynamic properties of new medications, contributing to the advancement of therapeutic options for a range of diseases and conditions.
Used in Chiral Compound Synthesis:
Due to its specific stereochemistry, (2S,5S)-5-hydroxy-2-methylpiperidine is also used in the synthesis of chiral compounds, which are essential in many biological processes and have distinct effects in the body. The ability to produce enantiomerically pure compounds is crucial for the development of drugs with fewer side effects and greater therapeutic potential.
Used in Research and Development:
In research and development settings, (2S,5S)-5-hydroxy-2-methylpiperidine is utilized as a model compound to study the effects of stereochemistry on molecular properties and reactivity. This knowledge can be applied to the design of new synthetic routes and the optimization of existing processes, ultimately contributing to the advancement of chemical science and technology.
Check Digit Verification of cas no
The CAS Registry Mumber 150197-75-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,0,1,9 and 7 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 150197-75:
(8*1)+(7*5)+(6*0)+(5*1)+(4*9)+(3*7)+(2*7)+(1*5)=124
124 % 10 = 4
So 150197-75-4 is a valid CAS Registry Number.
150197-75-4Relevant articles and documents
Bis(difluoromethyl)trimethylsilicate Anion: A Key Intermediate in Nucleophilic Difluoromethylation of Enolizable Ketones with Me3SiCF2H
Chen, Dingben,Ni, Chuanfa,Zhao, Yanchuan,Cai, Xian,Li, Xinjin,Xiao, Pan,Hu, Jinbo
, p. 12632 - 12636 (2016)
A pentacoordinate bis(difluoromethyl)silicate anion, [Me3Si(CF2H)2]?, is observed for the first time by the activation of Me3SiCF2H with a nucleophilic alkali-metal salt and 18-crown-6. Further study on its reactivity by tuning the countercation effect led to the discovery and development of an efficient, catalytic nucleophilic difluoromethylation of enolizable ketones with Me3SiCF2H by using a combination of CsF and 18-crown-6 as the initiation system. Mechanistic investigations demonstrate that [(18-crown-6)Cs]+[Me3Si(CF2H)2]?is a key intermediate in this catalytic reaction.
Discovery of piperidine ethers as selective orexin receptor antagonists (SORAs) inspired by filorexant
Raheem, Izzat T.,Breslin, Michael J.,Bruno, Joseph,Cabalu, Tamara D.,Cooke, Andrew,Cox, Christopher D.,Cui, Donghui,Garson, Susan,Gotter, Anthony L.,Fox, Steven V.,Harrell, C. Meacham,Kuduk, Scott D.,Lemaire, Wei,Prueksaritanont, Thomayant,Renger, John J.,Stump, Craig,Tannenbaum, Pamela L.,Williams, Peter D.,Winrow, Christopher J.,Coleman, Paul J.
, p. 444 - 450 (2015/01/30)
Highly selective orexin receptor antagonists (SORAs) of the orexin 2 receptor (OX2R) have become attractive targets both as potential therapeutics for insomnia as well as biological tools to help further elucidate the underlying pharmacology of the orexin signaling pathway. Herein, we describe the discovery of a novel piperidine ether 2-SORA class identified by systematic lead optimization beginning with filorexant, a dual orexin receptor antagonist (DORA) that recently completed Phase 2 clinical trials. Changes to the ether linkage and pendant heterocycle of filorexant were found to impart significant selectivity for OX2R, culminating in lead compound PE-6. PE-6 displays sub-nanomolar binding affinity and functional potency on OX2R while maintaining >1600-fold binding selectivity and >200-fold functional selectivity versus the orexin 1 receptor (OX1R). PE-6 bears a clean off-target profile, a good overall preclinical pharmacokinetic (PK) profile, and reduces wakefulness with increased NREM and REM sleep when evaluated in vivo in a rat sleep study. Importantly, subtle structural changes to the piperidine ether class impart dramatic changes in receptor selectivity. To this end, our laboratories have identified multiple piperidine ether 2-SORAs, 1-SORAs, and DORAs, providing access to a number of important biological tool compounds from a single structural class.
