522608-86-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzyl-3-azabicyclo[3.2.1]octan-8-ol is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique structure and properties allow it to serve as a key building block in the development of novel therapeutic agents.
Used in Organic Chemistry Research:
3-Benzyl-3-azabicyclo[3.2.1]octan-8-ol is utilized as a research compound in organic chemistry, enabling scientists to explore its reactivity, stability, and potential applications in the synthesis of complex organic molecules. Its unique structure provides opportunities for the development of new synthetic methodologies and the discovery of novel chemical reactions.
Used in Drug Design and Development:
3-Benzyl-3-azabicyclo[3.2.1]octan-8-ol is employed as a starting material or a key component in the design and development of new drugs. Its pharmacological properties and versatile chemical structure make it a valuable asset in the creation of innovative therapeutic agents targeting various diseases and medical conditions.
Used in Medicinal Chemistry:
3-Benzyl-3-azabicyclo[3.2.1]octan-8-ol is applied in medicinal chemistry for the optimization of drug candidates and the improvement of their pharmacokinetic and pharmacodynamic properties. Its unique features can be leveraged to enhance the potency, selectivity, and safety of new drug molecules.

Upstream product

• 83507-33-9 3-benzyl-3-aza-bicyclo[3.2.1]octan-8-one 
• 882188-60-5 3-benzyl-3-azabicyclo[3.2.1]octan-8-ol 
• 521944-15-0 N-benzyl-3-azabicyclo[3.2.1]octan-8α-ol 
• 521944-35-4 N-benzyl-3-azabicyclo[3.2.1]octane-8α-yl trifluoromethanesulfonate 

Downstream Products

• 866615-21-6 N-benzyl-8β-[2-propoxy-4-(trifluoromethyl)phenoxy]-3-azabicyclo[3.2.1]octane 
• 934001-71-5 3-azabicyclo[3.2.1]octan-8-ol 
• 521944-35-4 N-benzyl-3-azabicyclo[3.2.1]octane-8α-yl trifluoromethanesulfonate 

Relevant academic research and scientific papers

PROGRANULIN MODULATORS AND METHODS OF USING THE SAME

Provided herein are compounds that modulate progranulin and methods of using the compounds in progranulin-associated disorders, such as Frontotemporal dementia (FTD).

PROCESS FOR PRODUCTION OF CIS-3-SUBSTITUTED-3- AZABICYCLO[3.2.1]OCTAN-8-OL DERIVATIVE

There are provided, according to the present invention, a method for producing a cis-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivative, the method characterized in that a trans-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivative or a mixture of the trans- and cis-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivatives is isomerized in the presence of an aluminum compound represented by a formula Al(OR1)3 (wherein R1 represents a hydrocarbon group in which a carbon atom having an oxygen atom bonded thereto is a secondary carbon atom). In the process, a ketone compound may be further added, in addition to the aluminum compound.

PROCESS FOR PRODUCTION OF AZABICYCLOALKANOL DERIVATIVE

The object is to produce an azabicycloalkanol derivative, particularly a cis-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivative which is a useful intermediate for agricultural chemicals or pharmaceutical agents, with a good yield and at an industrially low cost. A diastereomer of an azabicyclo-C6-10-alkanol derivative having a methyne substituted a hydroxyl group as an asymmetric carbon (e.g., a trans-3-substituted-3-azabicyclo[3.2.1]-8-ol derivative) is isomerized in the presence of a transition metal complex, thereby producing an excess amount of a thermodynamically more stable one of diastereomers (e.g., a cis-3-substituted-3-azabicyclo[3.2.1]-8-ol derivative). In this manner, a thermodynamically more stable one of diastereomers of the azabicyclo-C6-10-alkanol derivatives can be produced.

Synthesis and pharmacology of site specific cocaine abuse treatment agents: 8-substituted isotropane (3-azabicyclo[3.2.1]octane) dopamine uptake inhibitors

A series of 8-substituted-3-azabicyclo[3.2.1] octanes (isotropanes) were synthesized and tested for inhibitor potency using [3H]WIN 35,428 binding at the dopamine (DA) transporter, [3H]citalopram binding at the serotonin (5-HT) transporter, and [3H]DA uptake assays. The synthesis started with a Mannich condensation of cyclopentanone, benzylamine, and fomaldehyde to afford N-benzyl-3-azabicyclo [3.2.1]octan-8-one (6). The 8-phenyl group was introduced by Grignard addition to ketone 6 or nucleophilic displacement via a triflate of the corresponding alcohol 7a. The 8β-phenyl-8α-alcohols from Grignard addition generally have low affinity for the two transporters and do not effectively inhibit the uptake of [3H]DA. The 8β-phenyl compound (14) without the hydroxyl group at C-8 was much more potent (22-fold) for [3H]WIN 35,428 binding inhibition than the corresponding 8β-phenyl-8α-hydroxy compound (7a). The 8α-phenyl compound 8a was almost as potent as cocaine in binding to the DA transporter (IC50 = 234 nM vs 159 nM for cocaine), whereas the C-8 epimer, compound 14, was somewhat less potent (IC50 = 785 nM). The lower potency of 14 (β-orientation of 8-phenyl group) as compared to 8a (α-orientation) was unexpected, based on modeling studies comparing the new compounds to WIN 35,065-2, an analogue of cocaine. The benzhydryl ethers at C-8 (17), analogous to the benztropines, had better selectivity than the corresponding phenyl compounds, 8a and 14, for the DA transporter as compared to the 5-HT transporter. The isotropane and benzisotropine analogues seem to bind in a manner that is more similar to that of the benztropine compounds 5 rather than those of cocaine and WIN 35,065-2.