4-N-Boc-aminocyclohexanone
[CAS# 179321-49-4]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 4-N-Boc-aminocyclohexanone
• Synonyms: (4-Oxocyclohexyl)carbamic acid tert-butyl ester
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.27
• CAS Registry Number: 179321-49-4
• EC Number: 672-405-6
• SMILES: CC(C)(C)OC(=O)NC1CCC(=O)CC1

Properties

• Melting point: 114-118 °C

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H335--H400
• Safety Statements: P261-P271-P273-P304+P340-P319-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-N-Boc-aminocyclohexanone, also known as tert-butyl (4-oxocyclohexyl) carbamate, is a valuable organic chemical compound, particularly useful as a pharmaceutical synthesis intermediate and a versatile building block in the development of complex molecules. The development of 4-N-Boc-aminocyclohexanone stems from the need to create stable functionalized intermediates for multi-step organic syntheses. The tert-butyloxycarbonyl (Boc) group was introduced in the 1950s to provide a protecting function that allows for selective reactions on other parts of the molecule. Its combination with aminocyclohexanone was intended to produce intermediates that can be easily manipulated in synthetic pathways.

4-N-Boc-aminocyclohexanone The cyclohexanone core is a six-membered ring containing a carbonyl group at position 4, with the nitrogen atom at position 4 protected by a tert-butylcarbamate (Boc) group. It is a white to off-white crystalline solid that is soluble in common organic solvents such as dichloromethane and ethanol; slightly soluble in water.

4-N-Boc-aminocyclohexanone is a key intermediate in the synthesis of various pharmaceuticals. Its Boc-protected amine can be selectively deprotected, allowing for subsequent functionalization to produce active pharmaceutical ingredients (APIs). The compound can be used in the design of prodrugs, where the Boc group is cleaved in vivo to release the active drug, thereby improving the bioavailability and stability of the drug.

In organic synthesis, 4-N-Boc-aminocyclohexanone can be used as a building block for the construction of complex molecules. Its structure allows the introduction of other functional groups, facilitating the development of a variety of chemical entities. The Boc group can be selectively removed under acidic conditions, providing a strategy to protect the amine functional group during multi-step synthesis and allow for selective modification at other sites.

The compound is used in the synthesis of functional polymers, where amine groups are introduced that can interact with other ingredients, thereby enhancing the material's properties such as adhesion, flexibility, or chemical resistance. 4-N-Boc-aminocyclohexanone can be used in surface modification techniques to introduce amine functional groups to the surface, facilitating the development of advanced materials for coatings, adhesives, and biomedical applications.

Researchers use 4-N-Boc-aminocyclohexanone to study the mechanisms of reactions involving amine protection and deprotection, helping to understand the behavior of protecting groups under different conditions. The compound is used in exploratory studies to develop new synthetic methods and reactions, expanding the toolkit available for creating complex molecules in both academic and industrial settings.

In the agrochemical industry, 4-N-Boc-aminocyclohexanone is used as an intermediate in the synthesis of biologically active compounds that are useful as herbicides, fungicides, and insecticides.

References

2024. Novel pharmacologic inhibition of lysine-specific demethylase 1 as a potential therapeutic for glioblastoma. Cancer Gene Therapy.
DOI: 10.1038/s41417-024-00847-8

2019. Synthesis of SIPI 6398. Synfacts.
DOI: 10.1055/s-0039-1690627

2012. Synthesis and structure-activity relationship studies on novel 8-amino-3-[2-(4-fluorophenoxy)ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione derivatives as anticonvulsant agents. Medicinal Chemistry Research.
DOI: 10.1007/s00044-012-0265-x