646055-63-2

Usage

Uses

Used in Pharmaceutical Synthesis:
7-Boc-1,7-diaza-spiro[4.4]nonane is used as a key building block for the synthesis of pharmaceuticals, leveraging its versatility as a chiral auxiliary. This attribute is crucial for the development of enantiomerically pure drugs, which are essential for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Organic Synthesis:
In the field of organic synthesis, 7-Boc-1,7-diaza-spiro[4.4]nonane is utilized as a valuable tool due to its Boc protecting group, which facilitates controlled reactions under mild conditions. This feature is particularly beneficial for the synthesis of complex organic molecules where protecting groups are necessary to prevent unwanted side reactions.
Used in Stereoselective Compound Preparation:
7-Boc-1,7-diaza-spiro[4.4]nonane is employed as a component in the preparation of stereoselective compounds, capitalizing on its unique spirocyclic structure. The stereochemistry of molecules is critical in determining their biological activity, making 7-Boc-1,7-diaza-spiro[4.4]nonane an important asset in the creation of molecules with specific biological targets and properties.
Overall, 7-Boc-1,7-diaza-spiro[4.4]nonane is a multifaceted compound with applications across various industries, primarily due to its structural features and synthetic utility in creating pharmaceuticals and complex organic molecules with high stereoselectivity.

InChI:InChI=1/C12H22N2O2/c1-11(2,3)16-10(15)14-8-6-12(9-14)5-4-7-13-12/h13H,4-9H2,1-3H3

Upstream product

• 1510865-62-9 tert-butyl 3-(2-tosylhydrazono)-pyrrolidine-1-carboxylate 
• 646055-62-1 tert-butyl 6-benzyl-2,6-diazaspiro [4.4]nonane-2-carboxylate 

Downstream Products

• 1158749-77-9 1-methyl-1,7-diazaspiro[4,4]nonane 

Relevant academic research and scientific papers

Construction of NH-Unprotected Spiropyrrolidines and Spiroisoindolines by [4+1] Cyclizations of γ-Azidoboronic Acids with Cyclic N-Sulfonylhydrazones

The reactions of N-sulfonylhydrazones derived from cyclic ketones with γ-azidopropylboronic acid and 2-(azidomethyl)phenylboronic acid give rise to spirocyclic pyrrolidines and spiroisoindolines, respectively. The reactions proceed without the need of any transition-metal catalyst through a domino process that comprises the formation of a Csp3-C and a Csp3-N bond of the former hydrazonic carbon. The scope of the reaction has been explored by the preparation of over 50 examples of NH-unprotected spirocyclic derivatives. Importantly, this methodology could be applied for the preparation of alkaloid steroids from steroid N-tosylhydrazones.

Discovery of a novel bicyclic compound, DS54360155, as an orally potent analgesic without mu-opioid receptor agonist activity

We synthesized derivatives of a natural alkaloid, conolidine, and evaluated these derivatives in the acetic acid-induced writhing test and formalin test in ddY mice after oral administration. As a result, we identified (5S)-6-methyl-1,3,4,5,6,8-hexahydro-7H-2,5-methano[1,5]diazonino[7,8-b]indol-7-one sulfate salt, 15a (DS54360155), with a unique and original bicyclic skeleton, as an analgesic more potent than conolidine. Moreover, 15a did not exhibit mu-opioid receptor agonist activity.

THE USE OF N-ARYL DIAZASPIRACYCLIC COMPOUNDS IN THE TREATMENT OF ADDICTION

Compounds, compositions and methods for treating drug addiction, nicotine addiction, and/or obesity are disclosed. The compounds are N-aryl diazaspirocyclic compounds, bridged analogs of N-heteraryl diazaspirocyclic compounds, or prodrugs or metabolites of these compounds. The aryl group can be a five- or six-membered heterocyclic ring (heteroaryl). The compounds are effective at inhibiting dopamine production and/or secretion, and accordingly are effective at inhibiting the physiological "reward" process that is associated with ingestion of nicotine and/or illicit drugs. The compounds and compositions can be administered in effective amounts to inhibit dopamine release, wihout resulting in appreciable adverse side effects (e.g., side effects such as significant increases in blood pressure and heart rate, significant negative effects upon the gastro-intestinal tract, and significant effects upon skeletal muscle).