3-Azaspiro[5.5]undecan-9-one, 3-(phenylmethyl)-

3-Azaspiro[5.5]undecan-9-one, 3-(phenylmethyl)- serves as a highly versatile spirocyclic building block for medicinal chemistry, enabling the introduction of a well‑defined three‑dimensional motif into lead structures where phenylpiperidine fragments need to be replaced with a more rigid, metabolically stable scaffold. The ketone handle of 3-Azaspiro[5.5]undecan-9-one, 3-(phenylmethyl)- readily undergoes reductive amination, Grignard addition, and Wittig chemistry, allowing rapid diversification at the 9‑position while maintaining the spiro‑architecture intact. 3-Azaspiro[5.5]undecan-9-one, 3-(phenylmethyl)- has found application in the synthesis of novel chemokine receptor antagonists, muscarinic receptor ligands, and central nervous system drug candidates where tuning the dihedral angle between the aromatic ring and the basic nitrogen is critical for potency and selectivity. In addition, 3-Azaspiro[5.5]undecan-9-one, 3-(phenylmethyl)- is frequently employed as a key starting material for parallel library synthesis aimed at exploring structure‑activity relationships around the spiro‑junction, offering a high fraction of sp³ hybridized carbons that correlates with improved clinical success rates.

Product Parameters

Quality Assurance at Cosperpharm

Each batch undergoes:

● Gas chromatography (GC) – purity ≥97.0%

● Non‑aqueous titration – purity ≥97.0%

● Refractive index – confirmatory analysis

● ¹H NMR – structural verification

● Appearance – colorless to light yellow to light orange clear liquid

A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.

Product Advantages

1.Conformationally restricted spiro‑architecture: The spiro[5.5]undecane core locks the benzyl‑bearing nitrogen and the ketone‑containing ring into a near‑orthogonal orientation. This rigidification eliminates the conformational flexibility of typical phenylpiperidines, enabling medicinal chemists to probe precise spatial requirements of a target binding pocket and often resulting in improved selectivity over off‑target receptors.

2.Reactive ketone handle for late‑stage diversification: The 9‑ketone is ideally positioned for stereoselective reductive amination, organometallic addition, and olefination reactions, allowing rapid generation of analogs with substituted amines, alcohols, or alkenes at the distal end of the spiro system without disturbing the N‑benzyl motif.

3.Optimised lipophilicity and permeability: The benzyl group confers a balanced lipophilicity (clogP ~2.9) that falls within the favorable range for CNS drug candidates, while the absence of hydrogen bond donors maintains a low tPSA, supporting passive membrane permeability.

4.Synthetic accessibility: The structure can be constructed in a few high‑yielding steps from commercially available 4‑piperidone derivatives, making it cost‑effective to obtain in multi‑gram to kilogram quantities for early‑stage medicinal chemistry campaigns.

FAQ

Q1: What is the physical state of 3-Azaspiro[5.5]undecan-9-one, 3-(phenylmethyl)-?

A: It is most commonly obtained as a pale yellow to light brown low‑melting solid or viscous oil. If crystallization is slow, it may remain as a super‑cooled oil at room temperature. Gentle warming (40–50 °C) usually converts it to a freely flowing liquid that is easier to transfer.

Q2: What is the solubility profile?

A: The compound is freely soluble in common organic solvents such as dichloromethane, tetrahydrofuran, ethyl acetate, and toluene. It shows limited solubility in hexane and water. For aqueous reactions, stock solutions in DMSO or DMF are recommended.

Contact Us

Preparing to functionalise that spiro centre? Contact Cosperpharm for a sample of 3-Azaspiro[5.5]undecan-9-one, 3-(phenylmethyl)- and get your project moving with a building block that marries rigidity with reactivity. Our team is on standby to provide quotes, answer technical questions, and arrange overnight delivery to your lab. Let’s discuss how our intermediates can accelerate your discovery timeline.