tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate
[CAS# 1041026-70-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate
• Synonyms: 2,6-Diazaspiro[3.3]heptane-2-carboxylic acid 1,1-Dimethylethyl ester; ; 1,1-Dimethylethyl 2,6-diazaspiro[3.3]heptane-2-carboxylate; tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate
• Molecular Formula: C₁₀H₁₈N₂O₂
• Molecular Weight: 198.27
• CAS Registry Number: 1041026-70-3
• EC Number: 888-556-8
• SMILES: CC(C)(C)OC(=O)N1CC2(C1)CNC2

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 282.6±40.0 °C 760 mmHg (Calc.)^*
• Flash point: 124.7±27.3 °C (Calc.)^*
• Index of refraction: 1.525 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate is a chemical compound with significant potential in both synthetic chemistry and pharmaceutical development. It belongs to a class of compounds known as spiro compounds, which are characterized by having two or more rings that are connected at a single atom. Specifically, this compound is a member of the diazaspiro class, which incorporates nitrogen atoms into its bicyclic structure.

The structure of tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate features a spiro linkage between a piperidine-like nitrogen-containing ring and another ring that incorporates an ester functional group at the 2-position. This makes the compound a useful scaffold for further chemical modifications, enabling it to be adapted for various applications in the pharmaceutical industry.

The compound has found particular use in medicinal chemistry, where it is employed as a potential building block for the design of novel drug molecules. The nitrogen atoms in the spiro ring system provide sites for potential interactions with biological targets, making it an attractive candidate for the synthesis of molecules with biological activity. Additionally, the presence of the ester group makes the compound suitable for ester hydrolysis reactions, a feature often exploited in prodrug design, where the compound can be transformed into an active pharmaceutical ingredient upon enzymatic cleavage.

In terms of synthetic applications, the compound can serve as a key intermediate for the synthesis of a variety of functionalized spiro compounds. Its structural features make it a versatile molecule, and it has been used in the preparation of more complex structures with potential applications in both drug discovery and material science. The stability imparted by the tert-butyl group helps ensure that the compound remains resistant to degradation during synthesis and handling, making it useful in a wide range of synthetic processes.

Beyond its applications in organic synthesis, tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate has shown potential in the development of drugs targeting central nervous system disorders. The spirocyclic nature of the molecule, coupled with its nitrogen-containing heterocyclic structure, allows it to interact with a variety of receptors, enzymes, and other biological molecules. This has led to its investigation in a number of preclinical studies focused on neurological and psychiatric diseases, where it is considered for use as a lead compound for the development of drugs with novel mechanisms of action.

Furthermore, the unique spirocyclic structure also makes this compound an interesting candidate for incorporation into larger, more complex molecular architectures. Its ability to undergo selective functionalization at specific positions, particularly in medicinal chemistry, means it can be tailored to target a wide variety of biological systems. As such, research continues to explore its full potential in drug discovery, particularly for diseases where conventional drug development strategies have not yielded optimal outcomes.

In conclusion, tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate is a versatile chemical compound with significant potential in synthetic chemistry and pharmaceutical development. Its spirocyclic structure, combined with functional groups like the ester, makes it useful in both the design of drug molecules and the synthesis of complex organic compounds. The ongoing investigation into its pharmacological properties underscores its potential as a valuable tool in the development of novel therapeutic agents.

References

2023. Increased rigidity and bioisosteric replacement in the design, synthesis and preliminary evaluation of novel, functionalized 3,3-dialkyl-γ-butyrolactones as sigma-2 ligands. Medicinal Chemistry Research, 32(12).
DOI: 10.1007/s00044-023-03182-z

2022. Synthesis and evaluation of cyclic diamino benzamide based D3 receptor ligands. Medicinal Chemistry Research, 31(2).
DOI: 10.1007/s00044-021-02845-z