tert-Butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate

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Cat Number

INT144282371

CAS Number

144282-37-1

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Product Detail Description Customer Q&A

CAS Number

144282-37-1

EINECS

1806241-263-5

Storage

2-8℃

Synonyms

Carbamic acid, [(7S)-5-(phenylmethyl)-5-azaspiro[2.4]hept-7-yl]-, 1,1-dimethylethyl ester; [(7S)-5-(Phenylmethyl)-5-azaspiro[2.4]hept-7-yl]carbamic acid tert-butyl ester

Molecular Formula

C18H26N2O2

Molecular Weight

302.4

Smiles

CC(C)(C)OC(=O)N[C@@H]1CN(CC12CC2)CC3=CC=CC=C3

Appearance

White to off-white solid

Boiling Point

420.5℃

Relative Density

1.12

pKa

12.31

General Description

Tert-Butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate is a complex chiral organic building block featuring a spirocyclic framework. This compound consists of a 5-azaspiro[2.4]heptane core where the nitrogen atom is protected by a benzyl group and the chiral C7 position is functionalized with a tert-butoxycarbonyl (Boc) protected amine. It is a highly specialized intermediate used primarily in the synthesis of advanced pharmaceutical agents that require rigid, three-dimensional molecular geometries to achieve high biological specificity.

Mechanism of Action

As a synthetic intermediate, tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate functions as a scaffold for constructing rigidified proline or pyrrolidine analogs. The spiro[2.4]heptane ring system introduces significant conformational constraint, which can lock the molecule into a bioactive conformation, thereby increasing its binding affinity to target enzymes or receptors. The (S)-configuration at the C7 center ensures the correct stereochemical orientation, while the Boc and benzyl protecting groups allow for orthogonal deprotection, enabling selective chemical modifications at either the primary or secondary amine sites during complex multi-step synthesis.

Application

Tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate is predominantly utilized as a key intermediate in the development of potent antimicrobial agents, including specialized fluoroquinolones like Sitafloxacin. It is also employed in medicinal chemistry for the design of protease inhibitors and neurological drug candidates where a rigidified pyrrolidine ring is required to optimize pharmacokinetic properties.

Is tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate soluble in organic solvents?

Yes, tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate is highly soluble in common organic solvents such as dichloromethane, ethyl acetate, and methanol.

What is the function of the Boc group in tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate?

The Boc group in tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate serves as a temporary protecting group for the primary amine, which can be easily removed under acidic conditions.

How should tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate be stored?

Tert-butyl (S)-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)carbamate should be stored in a cool, dry area in a tightly sealed container, preferably under refrigeration to maintain its long-term stability.

Are technical documents like COA and SDS available?

Yes, every batch is supplied with a batch-specific Certificate of Analysis.