3-Azaspiro[5.5]undec-7-ene-3-carboxylic acid, 9-oxo-, phenylMethyl ester

3-Azaspiro[5.5]undec-7-ene-3-carboxylic acid, 9-oxo-, phenylMethyl ester is an advanced intermediate in the synthesis of biologically active spirocyclic compounds, including certain antiviral agents and kinase inhibitors. The α,β‑unsaturated ketone of 3-Azaspiro[5.5]undec-7-ene-3-carboxylic acid, 9-oxo-, phenylMethyl ester provides a reactive electrophilic site for Michael additions with amines, thiols, or stabilized carbanions, enabling rapid expansion of molecular complexity. By deprotecting the Cbz group of 3-Azaspiro[5.5]undec-7-ene-3-carboxylic acid, 9-oxo-, phenylMethyl ester via hydrogenolysis, the free piperidine is exposed and can be alkylated or acylated. Cosperpharm supplies 3-Azaspiro[5.5]undec-7-ene-3-carboxylic acid, 9-oxo-, phenylMethyl ester as a single, well‑characterized enantiomer or racemate, as needed, ensuring fidelity in stereochemically defined drug programs.

Product Parameters

Product Advantages

1. Spirocyclic Core – The spiro[5.5]undecane skeleton imparts three‑dimensionality and conformational restraint, increasing target selectivity.

2. Orthogonal Reactive Sites – The Cbz‑protected amine and the enone can be addressed independently through careful reaction order.

3. Michael Acceptor Enone – Allows conjugate addition, Robinson annulation, or Luche reduction to build further complexity.

4. Crystalline Solid – Easy to purify and handle; consistent lot‑to‑lot crystallinity ensures reproducible dissolution in reaction media.

5. Regulatory‑Friendly – Benzyl carbamate is a standard protecting group; its removal by hydrogenolysis is well‑established in API manufacturing.

Synthetic Route

A general synthesis of 3-Azaspiro[5.5]undec-7-ene-3-carboxylic acid, 9-oxo-, phenylMethyl ester involves the formation of the spirocyclic core through an intramolecular aldol condensation or a Robinson annulation of a 4‑piperidone derivative with methyl vinyl ketone, followed by Cbz protection of the piperidine nitrogen. Alternatively, the spiro ring can be constructed by a double Michael addition or a Diels‑Alder strategy. Cosperpharm’s optimized route ensures >98% purity without the des‑Cbz or over‑reduced by‑products.

Application Scenarios

1.Antiviral Protease Inhibitor Core

The spirocyclic enone is a warhead or a structural mimic of peptide substrates in certain viral proteases.

2.Kinase Inhibitor Scaffold

The spiro‑piperidine motif fills a hydrophobic pocket while the enone can be functionalized with hinge‑binding heterocycles.

3.Natural Product‑Like Library Synthesis

Serves as a key intermediate for generating spiro‑alkaloid‑like compounds for phenotypic screening.

4.Michael Addition Diversification

The enone reacts with diverse amines and thiols in a parallel fashion to create compound libraries.

5.Process Validation Studies

Well‑characterized solid form suitable for kilogram‑scale spirocyclization optimization.

Contact Us

If this Cbz‑protected spirocyclic enone fits into your medicinal chemistry roadmap, contact Cosperpharm’s advanced intermediates team — we can arrange for an analytical sample and discuss a custom scale‑up plan based on your project’s forecasted demand.