tert-Butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate

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Cat Number

INT127199444

CAS Number

127199-44-4

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Product Detail Description Customer Q&A

CAS Number

127199-44-4

Storage

Under inert gas at 2–8℃

Molecular Formula

C11H20N2O2

Molecular Weight

212.29

Smiles

C(OC(C)(C)C)(=O)N[C@@H]1C2(CC2)CNC1

Appearance

White to off-white solid

Boiling Point

329.0℃

Relative Density

1.09

pKa

12.39

General Description

Tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate is a high-purity chiral intermediate featuring a distinctive spirocyclic 5-azaspiro[2.4]heptane core. This compound consists of a pyrrolidine ring fused at a single carbon atom to a cyclopropyl ring, with a tert-butoxycarbonyl (Boc) protected primary amine at the (7R) position. Its rigid three-dimensional architecture makes it an essential scaffold in the synthesis of specialized pharmaceutical compounds where precise stereochemical orientation and conformational constraint are required to optimize biological activity.

Mechanism of Action

As a chiral building block, tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate functions by introducing a rigidified proline-like moiety into a molecular framework. The spirocyclic system restricts the rotational freedom of the pyrrolidine ring, which can significantly enhance the binding affinity and selectivity of the final drug molecule for its target receptor or enzyme. The (7R) configuration provides the specific spatial arrangement necessary for bioactivity, while the Boc protecting group allows for the selective release of the primary amine under acidic conditions, facilitating further coupling or substitution reactions during multi-step synthesis.

Application

Tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate is primarily utilized as a critical intermediate in the production of advanced fluoroquinolone antibiotics. It is employed in the development of APIs targeting complex bacterial infections and chronic metabolic conditions. Additionally, tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate serves as a specialized reagent in medicinal chemistry research for the creation of chiral libraries and the exploration of spirocyclic scaffolds in the design of novel protease inhibitors and central nervous system (CNS) agents.

How does the spirocyclic structure of tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate benefit drug design?

The spirocyclic ring system of tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate provides high structural rigidity, which helps lock the molecule into a bioactive conformation and improves metabolic stability.

Is tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate soluble in common solvents?

Yes, it is soluble in standard organic solvents such as dichloromethane, methanol, and ethyl acetate.

What are the recommended storage conditions for tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate?

It should be stored in a cool, dry place, ideally under refrigeration, in a tightly sealed container to ensure its chemical stability.

Does tert-butyl (7R)-5-azaspiro(2.4)heptan-7-ylcarbamate meet international industry standards?

Yes, our production follows rigorous quality control protocols that are fully compliant with international industry standards for high-purity pharmaceutical intermediates.