N-Boc-piperidine-3-methanol CAS 116574-71-1

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N-Boc-piperidine-3-methanol, also known as N-Boc-piperidin-3-methanol, is an organic compound commonly used as an intermediate in organic synthesis. Molecular formula C11H21NO3, CAS 116574-71-1, appears as a white or grayish white solid powder. Used in the modification and derivatization reactions of drug molecules and bioactive molecules. The ester groups in its structure can undergo a series of transformations, including reduction to aldehyde groups, hydroxyl groups, or preparation of amide compounds through amine ester exchange reactions.

In addition, the Boc group on the nitrogen atom can be easily removed to obtain the corresponding secondary amine compounds. It has a specific chemical structure and properties, and can also be used as a synthetic raw material or modifier for certain polymer materials. By introducing this compound, certain physical or chemical properties of the material can be improved, such as increased heat resistance, chemical corrosion resistance, or enhanced mechanical strength.

1-Boc-3-hydroxymethylpiperidine (N-Boc-piperidine-3-methanol) plays a crucial role in the synthesis and modification of bioactive molecules due to its unique chemical structure and properties. This compound not only serves as a key intermediate in organic synthesis, but also has broad application prospects in the fields of medicinal chemistry and materials science due to its hydroxyl and Boc protecting groups.

The molecular formula of N-Boc-piperidine-3-methanol is C11H21NO3, with a molecular weight of 215.29. The hydroxyl and Boc (tert butoxycarbonyl) protecting groups in its structure endow the compound with unique chemical properties. Hydroxyl groups can participate in various chemical reactions, such as esterification, etherification, amination, etc., to generate compounds with different biological activities. The Boc protecting group can protect the nitrogen atom during the reaction process, avoiding unnecessary side reactions, and can also be easily removed in subsequent steps to restore the reactivity of the nitrogen atom.

Application of 1-Boc-3-hydroxymethylpiperidine in the synthesis of bioactive molecules

 

Modification and derivatization of drug molecules:
1-Boc-3-hydroxymethylpiperidine can be used as a starting material for drug molecule modification. By introducing different functional groups, drug derivatives with specific biological activities can be synthesized.

For example, through esterification reactions, carboxylic acid compounds can be combined with the hydroxyl group of 1-Boc-3-hydroxymethylpiperidine to form ester compounds, which often have better bioavailability and pharmacokinetic properties.

 

Construction of bioactive molecules:
1-Boc-3-hydroxymethylpiperidine can also serve as a key fragment for constructing bioactive molecules. By coupling reactions with other compounds, biologically active molecules with complex structures can be synthesized. For example, when synthesizing compounds with anti-tumor activity, 1-Boc-3-hydroxymethylpiperidine can be coupled with compounds containing aromatic or heterocyclic rings to generate compounds with specific pharmacophores. These compounds have shown significant anti-tumor activity in both in vitro and in vivo experiments.

 

Synthesis of Chiral Compounds:
1-Boc-3-hydroxymethylpiperidine can also be used as a synthetic material for chiral compounds. Chiral compounds with specific stereoconfigurations can be synthesized through methods such as asymmetric synthesis or stereoselective reduction. These chiral compounds have important application value in drug development, as the efficacy and toxicity of many drugs are closely related to their stereoisomers.

Specific examples

Synthesis of compounds with anti-tumor activity

Researchers have synthesized a series of compounds with anti-tumor activity using 1-Boc-3-hydroxymethylpiperidine as a key intermediate. These compounds combine with 1-Boc-3-hydroxymethylpiperidine through specific chemical reactions to form compounds with specific pharmacophores. In vitro experiments, these compounds showed significant inhibitory activity against various tumor cell lines. Further research indicates that these compounds exert anti-tumor effects by inhibiting tumor cell proliferation and inducing tumor cell apoptosis.

Synthesis of compounds with antidepressant activity

1-Boc-3-hydroxymethylpiperidine can also be used to synthesize compounds with antidepressant activity. By a specific chemical reaction, compounds containing antidepressant active groups were combined with 1-Boc-3-hydroxymethylpiperidine to generate new candidate compounds for antidepressant drugs. These compounds exhibit significant antidepressant activity in animal models with minimal side effects. These research findings provide new ideas and methods for the development of antidepressant drugs.

Synthesis of compounds with anti-inflammatory activity

Inflammation is a defense response of the human body against injury or infection, but excessive inflammation can lead to tissue damage and disease. Researchers have synthesized a series of compounds with anti-inflammatory activity using 1-Boc-3-hydroxymethylpiperidine as a key intermediate. These compounds exert anti-inflammatory effects by inhibiting the release of inflammatory mediators and reducing the infiltration of inflammatory cells. In animal models, these compounds have shown significant therapeutic effects on various inflammatory diseases.

Synthesis of compounds with antihypertensive activity

Hypertension is a common chronic disease that poses a serious threat to human health. Researchers have synthesized a series of compounds with antihypertensive activity using 1-Boc-3-hydroxymethylpiperidine as a key intermediate. These compounds lower blood pressure by inhibiting the activity of angiotensin-converting enzyme. In animal experiments, these compounds showed significant antihypertensive effects on hypertensive model animals with minimal side effects. These research findings provide new ideas and methods for the development of antihypertensive drugs.

In depth analysis of N-Boc-piperidine-3-methane impurity spectrum: top-level analytical technology matrix

N-Boc-piperidine-3-methanol (1-Boc-3-hydroxymethylpiperidine) is an organic synthetic intermediate widely used in the modification of drug molecules and bioactive molecules. Its molecular formula is C ₁₁ H ₂₁ NO ∝, and its CAS number is 116574-71-1. This compound has a pyridine ring modified with an N-Boc protecting group as its core structure, and a 3-methylol group (- CH ₂ OH) as its active site, which can participate in various derivatization reactions. However, various impurities may be introduced during the synthesis process, including unreacted raw materials, intermediates, by-products, and degradation products, which may affect the safety, stability, and efficacy of the drug. 

The synthesis pathway and potential impurity sources of N-Boc-piperidine-3-methan

The industrial synthesis of N-Boc-piperidine-3-methane usually starts from N-Boc-3-piperidinecarboxylic acid ethyl ester and selectively reduces the ester group to generate the target product through lithium aluminum tetrahydroxide (LiAlH ₄). The reaction is carried out at room temperature, and the Boc protecting group (tert butoxycarbonyl) on the nitrogen atom should be retained due to steric hindrance, while the ester group on the ring is reduced to hydroxymethyl.

Classification of Potential Impurities Sources
According to the mechanism of impurity generation, it can be divided into the following four categories:

Matrix construction of impurity mass spectrometry analysis technology

Multiple analytical techniques need to be integrated to form a complementary detection system for the impurity characteristics of N-Boc-piperidin-3-methanol. Construct a technology matrix from three dimensions: separation technology, identification technology, and quantitative technology:

01.Separation techniques: High performance liquid chromatography (HPLC) and gas chromatography (GC)

Reversed phase high performance liquid chromatography (RP-HPLC)

Application Scenario:

Separation of principal components and polar impurities (such as residual raw materials and hydrolysis products)
Gradient elution program optimization:
Initial conditions: 5% acetonitrile/water (containing 0.1% formic acid)
Gradient: 5-95% acetonitrile, 20 minutes
Detection wavelength: 210 nm (carbonyl absorption)

Gas Chromatography (GC)

Application Scenario:

Quantitative analysis of volatile impurities (such as solvent residues, quenchers)
Headspace injection (HS-GC) conditions:
Equilibrium temperature: 80 ℃
Balance time: 30 minutes
Carrier gas: Nitrogen (flow rate: 2 mL/min)

02.Identification techniques: Mass spectrometry (MS) and nuclear magnetic resonance (NMR)

Liquid chromatography-mass spectrometry (LC-MS)

Application Scenario:

Structural inference of unknown impurities (such as degradation products)
Ionization mode selection:
Positive ion mode (ESI+): detecting nitrogen-containing compounds (such as de Boc products)
Negative ion mode (ESI -): detecting carboxylic acid impurities

Nuclear Magnetic Resonance (NMR)

Application Scenario:

Absolute confirmation of impurity structure (such as stereoisomers)
Key nuclear signal analysis:
¹ H NMR: δ 1.46 (s, 9H, Boc-CH ∝), δ 3.94-3.31 (m, 3H, - CH ₂ OH)
¹ ³ C NMR: δ 80.2 (Boc-C), δ 62.1 (- CH ₂ OH)

03.Quantitative techniques: quantitative nuclear magnetic resonance (qNMR) and isotope dilution method

Quantitative Nuclear Magnetic Resonance (qNMR)

Application Scenario:

Absolute quantification of trace impurities (such as genotoxic impurities)
Experimental conditions:
Solvent: DMSO-d ₆
Internal standard: Dimethylsilane (DMS)
Pulse sequence: zg30

Isotope Dilution Mass Spectrometry (IDMS)

Application Scenario:

High precision quantification (such as chiral impurities)
Experimental procedure:
Synthesis of deuterated standards (such as N-Boc-3-piperidinemethanol d ∝)
Mix samples and standards in a 1:1 ratio
LC-MS/MS detection of isotopic peak area ratio

FAQ

What is the drug piperidine used for?

Whereas, piperidine acts as a potential clinical agent against cancers, such as breast cancer, prostate cancer, colon cancer, lung cancer, and ovarian cancer, when treated alone or in combination with some novel drugs.

How toxic is this piperidine?

EPA (1985) reported that piperidine is a strong local irritant that can cause permanent injury after a short exposure to small amounts. DASE (1980) reported that inhalation exposure causes sore throat, coughing, labored breathing, and dizziness.

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