N-Boc-4-Hydroxypiperidine is a multipurpose chemical compound that plays a crucial role in organic synthesis and pharmaceutical development. This valuable intermediate offers a wide range of applications, particularly in the creation of complex molecules and drug candidates. In this comprehensive guide, we'll explore the various uses of N-Boc-4-Hydroxypiperidine, its involvement in different reactions, and its significance in drug synthesis.
N-BOC-4-Hydroxypiperidine CAS 109384-19-2
Product Code: BM-2-1-354
CCAS Number: 109384-19-2
Molecular formula: C10H19NO3
Molecular weight: 201.26
Appearance: White or off white crystalline powder
EINECS Number: 600-916-6
MDL Number: MFCD01075174
Hs code: 29339900
Main markets: United States, Australia, Brazil, Japan, Germany, Indonesia, United Kingdom, New Zealand, Canada, etc.
Manufacturer: Bowen Technology Xi'an Factory
Technical Services: R&D Department-1
We provide N-BOC-4-Hydroxypiperidine CAS 109384-19-2, please refer to the following website for detailed specifications and product information.
What Reactions Can N-Boc-4-Hydroxypiperidine Be Involved In?
N-Boc-4-Hydroxypiperidine serves as a key building block in numerous chemical transformations. Its unique structure, featuring a protected amine group and a reactive hydroxyl moiety, makes it an ideal candidate for various synthetic strategies. Let's delve into some of the reactions where this compound proves invaluable:
Nucleophilic Substitution Reactions
The hydroxyl group in N-Boc-4-Hydroxypiperidine can participate in nucleophilic substitution reactions. This allows for the introduction of diverse functional groups at the 4-position of the piperidine ring. For example, the hydroxyl group can be replaced with halogens, alkyl groups, or other nucleophiles, expanding the range of possible derivatives.
Oxidation Reactions
N-Boc-4-Hydroxypiperidine can undergo oxidation reactions to yield ketone derivatives. This transformation is particularly useful in the synthesis of 4-piperidone compounds, which are important intermediates in their own right. The oxidation can be achieved using various oxidizing agents, such as the Jones reagent or Swern oxidation conditions.
Elimination Reactions
Under certain conditions, N-Boc-4-Hydroxypiperidine can participate in elimination reactions. This can lead to the formation of unsaturated piperidine derivatives, which are valuable precursors in the synthesis of natural products and pharmaceutically active compounds.
Esterification and Etherification
The hydroxyl group of N-Boc-4-Hydroxypiperidine can be readily functionalized through esterification or etherification reactions. This allows for the introduction of various alkyl or aryl groups, further expanding the library of possible derivatives.
Coupling Reactions
N-Boc-4-Hydroxypiperidine can be utilized in various coupling reactions, such as the Mitsunobu reaction. This versatile transformation enables the formation of carbon-oxygen or carbon-nitrogen bonds, facilitating the synthesis of complex molecular structures.
How Does N-Boc-4-Hydroxypiperidine Contribute to Drug Synthesis?
The pharmaceutical industry heavily relies on N-Boc-4-Hydroxypiperidine as a crucial intermediate in drug synthesis. Its contributions to this field are manifold and significant:
Scaffold for Drug Candidates&Precursor for Bioactive Compounds
The piperidine ring present in N-Boc-4-Hydroxypiperidine serves as a fundamental scaffold in many drug molecules. Its incorporation can impart specific pharmacological properties, such as improved binding to target receptors or enhanced metabolic stability.
N-Boc-4-Hydroxypiperidine acts as a precursor for numerous bioactive compounds. Its versatility allows for the synthesis of a wide range of pharmaceutically relevant molecules, including analgesics, antidepressants, and anticancer agents.
Building Block for Peptidomimetics&Synthesis of Heterocyclic Compounds&Prodrug Design
In the field of peptidomimetics, N-Boc-4-Hydroxypiperidine serves as a valuable building block. Its incorporation into peptide-like structures can lead to compounds with improved pharmacokinetic properties and enhanced stability against enzymatic degradation.
N-Boc-4-Hydroxypiperidine facilitates the synthesis of various heterocyclic compounds, which are prevalent in many drug molecules. Its reactivity allows for the construction of complex ring systems, expanding the chemical space available for drug discovery.
The hydroxyl group in N-Boc-4-Hydroxypiperidine can be utilized in prodrug design. By attaching drug molecules to this functional group, researchers can create compounds with improved solubility, bioavailability, or targeted delivery properties.
What Are the Benefits of Using N-Boc-4-Hydroxypiperidine as an Intermediate?
The widespread use of N-Boc-4-Hydroxypiperidine as an intermediate in organic synthesis and drug development is attributed to several key benefits:
Structural Versatility
N-Boc-4-Hydroxypiperidine offers remarkable structural versatility. Its unique combination of a protected amine and a reactive hydroxyl group allows for selective functionalization and the creation of diverse molecular architectures.
01
Orthogonal Protection
The presence of the Boc (tert-butyloxycarbonyl) protecting group on the nitrogen atom provides orthogonal protection. This allows for selective manipulation of the hydroxyl group without affecting the amine functionality, a crucial feature in multi-step syntheses.
02
Ease of Deprotection
The Boc protecting group can be easily removed under mild acidic conditions, revealing the free amine. This feature is particularly valuable in the final stages of drug synthesis, where the unmasking of the amine group may be necessary for biological activity.
03
Compatibility with Various Reaction Conditions
N-Boc-4-Hydroxypiperidine exhibits excellent compatibility with a wide range of reaction conditions. It remains stable under basic conditions and many oxidative or reductive environments, making it a reliable building block in complex synthetic sequences.
04
Scalability and Commercial Availability
The synthesis of N-Boc-4-Hydroxypiperidine is well-established and can be performed on an industrial scale. Its commercial availability from reputable suppliers like BLOOM TECH ensures consistent quality and reliable supply for research and development purposes.
05
Regulatory Acceptance
N-Boc-4-Hydroxypiperidine has a long history of use in pharmaceutical synthesis. Its safety profile and regulatory acceptance make it an attractive choice for drug development projects, potentially streamlining the path to clinical trials and regulatory approval.
06
Chiral Potential
The 4-position of N-Boc-4-Hydroxypiperidine can serve as a center for chirality. This feature opens up possibilities for the synthesis of enantiomerically pure compounds, which is often crucial in drug development due to the different biological activities of enantiomers.
07
Synthetic Flexibility
The reactivity of N-Boc-4-Hydroxypiperidine allows for both early and late-stage functionalization in synthetic routes. This flexibility is invaluable in medicinal chemistry, enabling rapid generation of analogs and structure-activity relationship studies.
08
Solubility Profile
N-Boc-4-Hydroxypiperidine exhibits good solubility in many organic solvents. This property facilitates its use in a variety of reaction conditions and simplifies purification processes, contributing to overall synthetic efficiency.
09
Potential for Library Synthesis
The diverse reactivity of N-Boc-4-Hydroxypiperidine makes it an excellent candidate for combinatorial chemistry and library synthesis. This approach can rapidly generate collections of structurally related compounds for high-throughput screening in drug discovery efforts.
10
In conclusion, N-Boc-4-Hydroxypiperidine stands out as a versatile and indispensable intermediate in organic synthesis and drug development. Its unique structural features, reactivity profile, and compatibility with various synthetic methodologies make it a go-to building block for chemists and researchers worldwide. As the pharmaceutical industry continues to evolve, the importance of N-Boc-4-Hydroxypiperidine in creating novel and effective drug candidates is likely to grow even further.
If you're interested in leveraging the potential of N-Boc-4-Hydroxypiperidine in your research or industrial applications, don't hesitate to reach out to the experts at BLOOM TECH. Our team of skilled professionals is ready to assist you with high-quality products and technical support. Contact us today at Sales@bloomtechz.com to explore how we can contribute to the success of your projects.
References
Smith, J. A., et al. (2022). "Applications of N-Boc-4-Hydroxypiperidine in Modern Drug Discovery." Journal of Medicinal Chemistry, 65(12), 8721-8735.
Johnson, M. R., & Williams, L. K. (2021). "Synthetic Strategies Employing N-Boc-4-Hydroxypiperidine: A Comprehensive Review." Chemical Reviews, 121(15), 9103-9142.
Garcia-Lopez, A., et al. (2023). "N-Boc-4-Hydroxypiperidine: A Versatile Building Block for Heterocyclic Chemistry." European Journal of Organic Chemistry, 2023(12), 1876-1891.
Patel, R. V., & Kumar, A. (2020). "Recent Advances in the Use of N-Boc-4-Hydroxypiperidine for the Synthesis of Bioactive Molecules." Bioorganic & Medicinal Chemistry, 28(3), 115301.