Chemical Identity and Structure

Benzyl N-(3-oxocyclopentyl)carbamate (SKU: B177002) is an organic compound featuring a five-membered carbocyclic ketone ring with an amine substituent at the 3-position protected as a benzyloxycarbonyl (Cbz) carbamate. The molecule thus presents two orthogonally reactive functional groups: a ketone carbonyl suitable for nucleophilic addition, reductive amination, condensation, and Wittig-type reactions, and a Cbz-protected amine that can be selectively deprotected under mild hydrogenolytic conditions (e.g., H₂/Pd-C, 1 atm, room temperature) without affecting most other common protecting groups.

The cyclopentanone scaffold confers a degree of conformational rigidity relative to acyclic analogs, a property valued in medicinal chemistry for controlling binding geometry in receptor-targeted drug candidates. The compound is typically encountered as a white to off-white crystalline solid and should be handled as a moderately reactive ketone intermediate.

Recommended Handling and Storage

Personal Protective Equipment: Use nitrile gloves, safety glasses, and a laboratory coat when handling benzyl N-(3-oxocyclopentyl)carbamate. Work in a well-ventilated fume hood, particularly during weighing operations, to minimise inhalation of fine particulates.

Storage Conditions: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from strong oxidising agents, reducing agents, and strong bases. A storage temperature of 2–8 °C or at room temperature under inert atmosphere (nitrogen or argon) is advisable to prevent slow oxidation or moisture uptake, both of which may degrade the compound over time. Confirm exact recommended storage conditions on the product Certificate of Analysis (CoA).

Stability: The Cbz group is stable to aqueous acidic and basic conditions within the mild pH range typically encountered in synthetic workups. The ketone may undergo slow aldol-type self-condensation under strongly basic conditions; avoid prolonged exposure to strong base in solution.

Disposal: Dispose of waste material and contaminated solvents in accordance with local institutional and governmental regulations for organic chemical waste.

Synthetic Applications and Reactivity

The bifunctional nature of benzyl N-(3-oxocyclopentyl)carbamate makes it a valuable building block in multi-step synthesis:

• Reductive Amination: The cyclopentanone ketone reacts readily with primary and secondary amines in the presence of reductants such as sodium cyanoborohydride or sodium triacetoxyborohydride, delivering 3-amino-substituted cyclopentylamine derivatives after Cbz deprotection.
• Nucleophilic Addition: Organolithium and Grignard reagents add to the ketone to afford tertiary alcohols, extending molecular complexity while the Cbz group remains intact.
• Cbz Deprotection: Hydrogenolysis under H₂/Pd-C releases the free amine quantitatively under mild conditions, enabling subsequent acylation, sulfonylation, or further elaboration.
• Wittig / Horner–Wadsworth–Emmons Olefination: The ketone serves as the carbonyl partner to install exocyclic alkenes for further functionalization.
• Enamine and Enol Formation: The alpha-methylene positions flanking the ketone are sufficiently activated for enolate chemistry, enabling alpha-alkylation or Michael addition sequences.

These reaction pathways make the compound particularly attractive in the preparation of constrained cyclopentyl amine scaffolds relevant to kinase inhibitors, protease inhibitors, and CNS-active drug candidates.

Quality, Purity and Analytical Characterisation

Researchers should verify compound identity and purity before use in sensitive synthetic sequences. Recommended analytical techniques include:

• ¹H and ¹³C NMR Spectroscopy: Confirms the presence of the Cbz aryl and OCH₂ signals, the cyclopentanone carbonyl, and the carbamate NH. Characteristic signals include the benzylic OCH₂ doublet near δ 5.1 ppm (¹H), the carbamate carbonyl near δ 156 ppm, and the ketone carbonyl near δ 218 ppm (¹³C).
• HPLC: Reverse-phase HPLC (C18 column, acetonitrile/water gradient) provides quantitative purity assessment. Aladdin Scientific provides a Certificate of Analysis (CoA) with each lot detailing purity and physical characterisation data.
• IR Spectroscopy: Strong carbonyl stretches expected near 1720 cm⁻¹ (ketone) and 1700 cm⁻¹ (carbamate C=O).
• Mass Spectrometry: ESI-MS or APCI-MS confirms molecular weight; the compound may be observed as [M+H]⁺ or [M+Na]⁺ adducts.

Always request and review the CoA for each lot. If purity is insufficient for a target application, consider recrystallisation from an appropriate solvent system or column chromatography prior to use.

Ordering, Packaging and Support

Benzyl N-(3-oxocyclopentyl)carbamate is available from Aladdin Scientific under SKU B177002. To place an order, contact your regional Aladdin Scientific representative or visit the Aladdin Scientific online catalogue. Bulk quantities and custom packaging may be available upon request; enquire with the sales team for lead times and pricing.

A Safety Data Sheet (SDS) is available for download from the Aladdin Scientific product page and should be reviewed prior to first use. For technical enquiries regarding synthetic application, analytical characterisation, or alternative reagents, contact the Aladdin Scientific technical support team.

All products are shipped with a Certificate of Analysis confirming identity, purity, and storage recommendations specific to the manufacturing lot.