Benzyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate CAS 790704-73-3 95% Purity Pharmaceutical Intermediate

1. Product Overview

Benzyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate (CAS: 790704-73-3), also known as 5-Cbz-1-oxa-5-azaspiro[2.4]heptane, is a Cbz-protected azaspirocyclic building block featuring a unique 1-oxa-5-azaspiro[2.4]heptane core with an embedded epoxide-like oxirane ring. With the molecular formula C₁₃H₁₅NO₃ and a molecular weight of 233.26 g/mol, this compound serves as a versatile intermediate in medicinal chemistry and organic synthesis. The Cbz protecting group allows mild deprotection to access the free secondary amine (1-oxa-5-azaspiro[2.4]heptane), while the rigid spiro architecture and oxirane moiety enable diverse functionalizations such as ring-opening reactions and scaffold elaboration for drug discovery.

2. Key Features and Advantages

• Cbz-Protected Amine: Enables clean, mild deprotection under hydrogenolysis (Pd/C, H₂) or alternative conditions to yield the free spirocyclic amine.

• Rigid Spiro Scaffold: 1-Oxa-5-azaspiro[2.4]heptane framework provides three-dimensional stereochemical control and improved metabolic stability in drug-like molecules.

• Reactive Oxirane Ring: Embedded ethylene oxide unit supports regioselective ring-opening with nucleophiles for linker installation (e.g., PROTACs, conjugates).

• High Purity: Supplied at 95%+ or 97%+ purity with CoA and NMR/HPLC verification for reliable multi-step synthesis.

• Versatile Handle: Compatible with standard peptide coupling, cross-coupling, and heterocycle functionalization workflows.

3. Main Applications

• Pharmaceutical Intermediates: Building block for piperidine-based APIs, CNS-active compounds, and spirocyclic drug scaffolds.

• PROTAC & Linker Chemistry: Oxirane ring allows attachment of payloads; spiro amine used as warhead or ligand connector.

• Medicinal Chemistry Research: Employed in library synthesis and structure–activity relationship (SAR) studies of azaspiro compounds.

• Fine Chemical Synthesis: Intermediate for chiral ligands, catalysts, and functional materials incorporating spiro architectures.

• Custom Synthesis: Suitable for milligram screening to gram-scale pilot runs in academic and CRO settings.

4. Technical Specifications

5. Storage and Handling

• Store in a cool, dry place protected from light and moisture. For best stability, keep at 0–8 °C or 2–8 °C in a tightly sealed container under inert atmosphere (N₂/Ar) if possible; the oxirane ring is sensitive to prolonged exposure to strong acids/bases and nucleophiles.

• Handle in a well-ventilated area or fume hood to avoid inhalation of vapors/dust.

• Use personal protective equipment: nitrile gloves, safety goggles, and lab coat.

• Avoid contact with strong acids, strong bases, and strong nucleophiles unless intended for controlled ring-opening or deprotection reactions.

• Keep container tightly closed when not in use. Follow standard laboratory hygiene practices; for Cbz hydrogenolysis, ensure proper hydrogen gas handling and Pd/C disposal protocols.

6. Safety Overview

This compound is a Cbz-protected spirocyclic amine containing an oxirane (epoxide-like) moiety; treat as potentially hazardous:

• Health Hazards: May cause skin irritation, eye irritation, and respiratory discomfort. Potential sensitizer; epoxy groups can be reactive toward biological nucleophiles.

• Environmental Precautions: Do not discharge into drains or waterways. Collect spillage and dispose of as hazardous chemical waste per local regulations.

• First Aid Measures:

• Skin Contact: Wash immediately with plenty of soap and water.

• Eye Contact: Rinse cautiously with water for several minutes; remove contact lenses if present; seek medical advice.

• Inhalation: Move to fresh air; if breathing difficulty occurs, administer oxygen and consult a physician.

• Ingestion: Rinse mouth; do NOT induce vomiting; seek immediate medical attention.

• Regulatory Note: For research and industrial use only, not for human or veterinary therapeutic use. SDS available upon request.