N-(tert-Butoxycarbonyl)-4-piperidone
[CAS# 79099-07-3]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: N-(tert-Butoxycarbonyl)-4-piperidone
• Synonyms: Boc-Piperidone; tert-Butyl 4-oxopiperidine-1-carboxylate
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.24
• CAS Registry Number: 79099-07-3
• EC Number: 616-664-5
• SMILES: CC(C)(C)OC(=O)N1CCC(=O)CC1

Properties

• Solubility: 5725 mg/L (25 ºC water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.481, Calc.^*
• Melting point: 73.98 ºC
• Boiling Point: 289.8±33.0 ºC (760 mmHg), Calc.^*, 276.77 ºC
• Flash Point: 129.1±25.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

N-(tert-Butoxycarbonyl)-4-piperidone, commonly known as Boc-4-piperidone, is a chemical compound that gained prominence in the mid-20th century with the development of modern peptide synthesis techniques. It is derived from 4-piperidone, with the introduction of a tert-butoxycarbonyl (Boc) protective group. The Boc group was first introduced by Robert Bruce Merrifield and others as a means to protect amine functionalities during peptide synthesis, allowing for sequential addition of amino acids. The synthesis of Boc-4-piperidone provided chemists with a valuable intermediate for constructing complex molecules, particularly in the field of medicinal chemistry.

One of the primary uses of Boc-4-piperidone is in the synthesis of peptides. The Boc group serves as a protective group for amines, preventing unwanted reactions during peptide bond formation. This allows for the sequential addition of amino acids to build up peptide chains. Once the synthesis is complete, the Boc group can be removed under acidic conditions, revealing the free amine group. This methodology is crucial in the production of synthetic peptides used in research, diagnostics, and therapeutics.

Boc-4-piperidone is a valuable intermediate in the synthesis of pharmaceutical compounds. Its structure allows for the introduction of various functional groups, facilitating the creation of complex molecular frameworks. It is often used in the synthesis of drug candidates, particularly those targeting the central nervous system, due to the piperidone moiety's relevance in medicinal chemistry. Compounds derived from Boc-4-piperidone have shown potential in treating conditions such as pain, depression, and neurodegenerative diseases.

The piperidone ring structure of Boc-4-piperidone is a versatile building block in heterocyclic chemistry. Heterocycles are ring structures containing atoms such as nitrogen, oxygen, or sulfur, and are fundamental components of many bioactive molecules. Boc-4-piperidone can undergo various chemical transformations, leading to the synthesis of a wide range of heterocyclic compounds. These compounds have applications in pharmaceuticals, agrochemicals, and materials science.

Beyond peptide synthesis, the Boc group in Boc-4-piperidone is used as a protective strategy in organic synthesis. The ability to temporarily protect amine groups while other reactions are carried out is invaluable in multi-step syntheses. This strategy is employed in the synthesis of complex natural products and other advanced organic molecules, enabling chemists to manipulate specific functional groups with precision.

In academic and industrial research laboratories, Boc-4-piperidone is used as a reagent and intermediate in the development of new chemical reactions and synthetic methodologies. Its role in exploring new pathways for building molecular complexity makes it a staple in organic synthesis research.

References

2024. Synthesis of monomers and polymers containing oligocationic groups. Russian Chemical Bulletin, 73(10).
DOI: 10.1007/s11172-024-4423-3

2024. Quantum chemical modelling, molecular docking, synthesis and experimental anti-microbial activity of 1,4-diazepan linked piperidine derivative. Future Journal of Pharmaceutical Sciences, 10(1).
DOI: 10.1186/s43094-024-00652-y

2023. Study on the synthesis technology of anticancer drug Gilteritinib fumarate. Russian Chemical Bulletin, 72(8).
DOI: 10.1007/s11172-023-3977-9