2-(3-(TERT-BUTOXYCARBONYL)-3-AZASPIRO[5.5]UNDECAN-9-YL)ACETIC ACID

2-(3-(TERT-BUTOXYCARBONYL)-3-AZASPIRO[5.5]UNDECAN-9-YL)ACETIC ACID is a spirocyclic amino acid surrogate widely employed in medicinal chemistry as a conformationally constrained building block. The Boc-protected amine of 2-(3-(TERT-BUTOXYCARBONYL)-3-AZASPIRO[5.5]UNDECAN-9-YL)ACETIC ACID is stable under the basic and neutral conditions commonly used for carboxylic acid derivatization, enabling sequential functionalization: the acid can be coupled to amines or alcohols while the Boc group remains intact, after which acidic deprotection reveals the free amine for further elaboration. 2-(3-(TERT-BUTOXYCARBONYL)-3-AZASPIRO[5.5]UNDECAN-9-YL)ACETIC ACID has found application in the synthesis of spiro-containing peptidomimetics, where the rigid scaffold replaces flexible amino acid linkers and enforces a specific turn geometry. Because 2-(3-(TERT-BUTOXYCARBONYL)-3-AZASPIRO[5.5]UNDECAN-9-YL)ACETIC ACID is a fully synthetic, crystalline intermediate available in multi-gram quantities, it serves as a reliable stock reagent for hit-to-lead campaigns and library synthesis.

Product Parameters

Product Advantages

1. Orthogonal protecting group strategy: The acid-labile Boc group on the piperidine nitrogen and the free carboxylic acid on the cyclohexane ring allow fully sequential chemical operations. The acid can be coupled under conditions that leave the Boc group unaffected, and subsequent treatment with TFA or HCl reveals the secondary amine for further derivatization, enabling efficient stepwise synthesis of complex spiro-containing structures.

2. Conformationally constrained scaffold: The spiro[5.5]undecane core eliminates rotational freedom between the two rings, enforcing a rigid spatial relationship between the protected amine and the carboxylic acid. This geometric predictability is valuable for designing peptidomimetics and receptor ligands where precise positioning of pharmacophoric elements is required.

3. Saturated, three-dimensional architecture: The all-carbon spiro framework, composed entirely of sp³-hybridized carbons, contributes to a high fraction of saturated carbons (Fsp³), a molecular property that has been correlated with improved clinical success rates and favorable physicochemical profiles.

4. Crystalline solid for ease of handling: The compound is a free-flowing powder or crystalline solid at ambient temperature, simplifying weighing, transfer, and storage in a laboratory setting.

Synthetic Route

The synthesis of spiro[5.5]undecane derivatives of this type is well-precedented in the patent and medicinal chemistry literature. A representative approach to constructing the 3-azaspiro[5.5]undecane core involves a double Michael addition or aldol condensation sequence starting from a 4-piperidone derivative and a suitably functionalized cyclohexanone or cyclohexenone building block, establishing the spiro junction. The acetic acid side chain can be introduced at the 9-position through Horner–Wadsworth–Emmons olefination followed by hydrogenation, or via other standard homologation methods. Boc protection of the piperidine nitrogen is typically achieved by treating the free amine with di-tert-butyl dicarbonate (Boc₂O) under basic conditions. Final hydrolysis of any ester intermediate yields the target carboxylic acid.

Storage Conditions

Store 2-(3-(TERT-BUTOXYCARBONYL)-3-AZASPIRO[5.5]UNDECAN-9-YL)ACETIC ACID in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C. Protect from moisture, light, and excessive heat. Allow the container to equilibrate to ambient temperature before opening to avoid condensation. When stored as recommended, the compound is typically stable for a period of at least one to two years. Avoid exposure to strong acids (which may prematurely cleave the Boc group), strong oxidizing agents, and open flames.

Contact Us

Working on a project that demands a rigid, bifunctional spiro building block? Reach out to Cosperpharm today to request a sample, obtain a current Certificate of Analysis, or discuss your specific requirements for 2-(3-(TERT-BUTOXYCARBONYL)-3-AZASPIRO[5.5]UNDECAN-9-YL)ACETIC ACID. We are ready to support your discovery chemistry with reliable supply and responsive technical service.