• 1. Optimisation of a triazolopyridine based histone demethylase inhibitor yields a potent and selective KDM2A (FBXL11) inhibitor
  Katherine S. England,Anthony Tumber,Tobias Krojer,Giuseppe Scozzafava,Stanley S. Ng,Michelle Daniel,Aleksandra Szykowska,KaHing Che,Frank von Delft,Nicola A. Burgess-Brown,Akane Kawamura,Christopher J. Schofield,Paul E. Brennan Med. Chem. Commun. 2014 5 1879

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Piperidines Piperidinecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Piperidines Piperidinecarboxylic acids and derivatives Piperidinecarboxylic acids

Introduction to Tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate (CAS No. 143900-44-1)

Tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate, identified by its Chemical Abstracts Service number CAS No. 143900-44-1, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the piperidine class, a heterocyclic amine characterized by a six-membered ring containing one nitrogen atom. The presence of a hydroxyl group at the 3-position and a tert-butyl ester group at the 1-position confers unique chemical properties that make it a valuable intermediate in the synthesis of biologically active molecules.

The stereochemistry of (3S)-configuration is particularly noteworthy, as it introduces chirality into the molecule. Chiral compounds are of paramount importance in drug development, where the enantiomeric form of a molecule can significantly influence its pharmacological activity, metabolic stability, and overall therapeutic efficacy. The synthesis and study of tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate have been central to understanding how structural modifications can enhance drug-like properties.

In recent years, advancements in computational chemistry and molecular modeling have enabled researchers to predict and rationalize the behavior of complex molecules like tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate. These computational tools have been instrumental in identifying potential binding interactions with biological targets, such as enzymes and receptors, which are critical for drug discovery. For instance, studies have demonstrated that the hydroxyl group at the 3-position can engage in hydrogen bonding with polar residues in protein active sites, while the tert-butyl ester moiety may contribute to hydrophobic interactions.

The pharmaceutical industry has shown considerable interest in tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate due to its potential utility as a building block for more complex drug candidates. Researchers have explored its incorporation into scaffolds designed for treating neurological disorders, cardiovascular diseases, and inflammatory conditions. Notably, piperidine derivatives have been widely investigated for their role in modulating neurotransmitter systems, particularly in the context of central nervous system (CNS) drugs.

One of the most compelling aspects of tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate is its versatility in synthetic chemistry. The tert-butyl ester group can be readily converted into other functional moieties through hydrolysis or transesterification reactions, allowing for the generation of diverse analogues. This flexibility has been leveraged in high-throughput screening campaigns to identify novel compounds with improved pharmacokinetic profiles.

The stereochemical integrity of (3S)-configuration is maintained throughout synthetic transformations through carefully optimized protocols that minimize racemization. This has been achieved by employing chiral auxiliaries or catalysts that facilitate enantioselective reactions. Such methodologies underscore the importance of precision in synthetic organic chemistry when dealing with chiral molecules.

Recent preclinical studies have highlighted the potential of derivatives inspired by tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate. For example, researchers have synthesized analogues that exhibit inhibitory activity against specific enzymes implicated in disease pathways. These studies not only validate the compound’s utility as a scaffold but also provide insights into structure-activity relationships that can guide future drug design efforts.

The role of tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate in medicinal chemistry extends beyond its use as an intermediate. It serves as a benchmark for evaluating new synthetic strategies and methodologies aimed at constructing complex chiral molecules efficiently. The compound’s well-documented properties make it an attractive candidate for teaching and training purposes in academic institutions.

As computational power continues to grow, so does our ability to predict the behavior of molecules like tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate in vitro and in vivo. Machine learning models trained on large datasets of chemical structures and biological responses are being increasingly used to accelerate drug discovery pipelines. These models can identify promising derivatives based on their predicted pharmacological properties, thereby reducing the time and cost associated with experimental screening.

The future prospects for tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate remain bright, with ongoing research exploring its potential applications in emerging therapeutic areas such as oncology and immunology. The compound’s unique structural features offer opportunities for designing next-generation drugs with enhanced target specificity and reduced side effects.

In conclusion, tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate (CAS No. 143900-44-1) represents a significant advancement in pharmaceutical chemistry. Its stereochemical purity, synthetic versatility, and biological relevance position it as a cornerstone compound for drug discovery efforts aimed at addressing unmet medical needs.

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