tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate
[CAS# 877399-74-1]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate
• Synonyms: 4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester
• Molecular Formula: C₁₉H₃₂BN₃O₄
• Molecular Weight: 377.29
• CAS Registry Number: 877399-74-1
• EC Number: 800-459-4
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)C3CCN(CC3)C(=O)OC(C)(C)C

Properties

• Melting point: 110-116 °C
• Boiling point: 492.8 °C (760 mmHg)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate is a sophisticated chemical compound notable for its unique structural features and wide range of applications. This substance combines a tert-butyl ester group, a pyrazole ring substituted with a boronate ester, and a piperidine ring. The integration of these functional groups renders the compound highly versatile in various chemical and pharmaceutical contexts.

The discovery of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate exemplifies advancements in the development of complex organic molecules with targeted functionalities. The synthesis of this compound typically involves the reaction of a piperidine derivative with a pyrazole-based boronate ester, followed by esterification with tert-butyl carboxylate. This process underscores significant progress in chemical synthesis, enabling the creation of highly functionalized molecules with potential for diverse applications.

One of the primary applications of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate is in medicinal chemistry. The compound's pyrazole and boronate ester groups are of considerable interest due to their potential interactions with biological targets. Pyrazole derivatives have been investigated for their therapeutic properties, including anti-inflammatory, antitumor, and antimicrobial activities. The addition of a boronate ester moiety enhances the compound's potential as a pharmaceutical agent by providing unique chemical properties, such as the ability to form reversible covalent bonds with biomolecules.

The boronate ester group in the molecule is particularly valuable in the context of chemical biology and drug development. Boron-containing compounds are known for their ability to participate in specific interactions with biological systems, such as inhibition of proteasomes or enzymes. The inclusion of a boronate ester group in tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate opens up possibilities for designing selective inhibitors or modulators of biological processes.

In addition to its pharmaceutical applications, the compound serves as an important intermediate in organic synthesis. The presence of both the pyrazole and boronate ester groups allows for further functionalization and modification, making it a valuable building block in the synthesis of more complex molecules. Its versatility as an intermediate underscores its significance in advancing synthetic organic chemistry and the development of novel materials.

The application of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate also extends to materials science. The compound's structural features may be exploited in the development of new polymers or materials with tailored properties. The ability to incorporate the boronate ester group into polymeric systems can lead to the creation of materials with unique mechanical, thermal, or optical characteristics.

Overall, tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate highlights the ongoing advancements in chemical synthesis and the exploration of complex molecules with specific functionalities. Its discovery reflects the continuous efforts to develop compounds with targeted applications across pharmaceuticals, materials science, and synthetic chemistry.

References

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2011. Synthesis of Crizotinib (PF-02341066). Synfacts, 7(12).
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