150197-75-4

Usage

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.

Upstream product

• 92599-79-6 β-acetoxy-α-hydroxy-N-(methoxycarbonyl)-α'-methylpiperidine 
• 92599-74-1 α,β-diacetoxy-N-(methoxycarbonyl)-α'-methylpiperidine 
• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 92599-87-6 5-Acetoxy-2-methyl-3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 1796-27-6 piperidine-1-carboxylic acid methyl ester 
• 92599-73-0 α,β-diacetoxy-N-(methoxycarbonyl)piperidine 
• 1314396-07-0 (±)-benzyl 5-hydroxy-2-methylpiperidine-1-carboxylate 
• 1314395-91-9 (±)-benzyl 2-methyl-5-oxopiperidine-1-carboxylate 
• 92599-78-5 β-acetoxy-α-hydroxy-N-(methoxycarbonyl)piperidine 
• 78999-63-0 α-methyl-piperidine 

Downstream Products

• 3197-43-1 (S)-(+)-2-methyl-1-(4-toluenesulfonyl)piperidine 

Relevant academic research and scientific papers

Bis(difluoromethyl)trimethylsilicate Anion: A Key Intermediate in Nucleophilic Difluoromethylation of Enolizable Ketones with Me3SiCF2H

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.

Investigation of orexin-2 selective receptor antagonists: Structural modifications resulting in dual orexin receptor antagonists

In an ongoing effort to explore the use of orexin receptor antagonists for the treatment of insomnia, dual orexin receptor antagonists (DORAs) were structurally modified, resulting in compounds selective for the OX2R subtype and culminating in the discovery of 23, a highly potent, OX2R-selective molecule that exhibited a promising in vivo profile. Further structural modification led to an unexpected restoration of OX1R antagonism. Herein, these changes are discussed and a rationale for selectivity based on computational modeling is proposed.

Discovery of piperidine ethers as selective orexin receptor antagonists (SORAs) inspired by filorexant

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.

ACETOXYLATION OF PIPERIDINE DERIVATIVES AT THE 3-POSITION. STEREOSELECTIVE SYNTHESIS OF PSEUDOCONHYDRINE AND N-METHYLPSEUDOCONHYDRINE

Anodic oxidation of N-methoxycarbonylpipridine derivatives in AcOH gave 2,3-diacetoxylated products, which were shown to be useful intermediates for the stereoselective synthesis of 3-hydroxypiperidine derivatives including pseudoconhydrine and N-methylpseudoconhydrine, the Conium alcaloids.