521944-15-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzyl-3-azabicyclo[3.2.1]octan-8-ol is utilized as a chemical intermediate for the synthesis of various pharmaceutical drugs. Its unique structure and functional groups enable the creation of diverse chemical compounds, making it a valuable component in drug development processes.
Used in Natural Product Synthesis:
In the field of natural product synthesis, 3-Benzyl-3-azabicyclo[3.2.1]octan-8-ol is employed as a building block. Its complex molecular structure allows for the construction of a variety of natural products, contributing to the advancement of natural product chemistry.
Used in Medicinal Chemistry Research:
3-Benzyl-3-azabicyclo[3.2.1]octan-8-ol is used as a target compound in medicinal chemistry research. Its potential biological activity and pharmacological properties make it a promising candidate for the discovery of new therapeutic agents and the exploration of novel mechanisms of action.
Used in Drug Discovery:
3-BENZYL-3-AZABICYCLO[3.2.1]OCTAN-8-OL is also used in drug discovery efforts, where its unique structural features and functional groups are leveraged to identify and develop new drug candidates with potential therapeutic applications.

Upstream product

• 83507-33-9 3-benzyl-3-aza-bicyclo[3.2.1]octan-8-one 

Downstream Products

• 521944-35-4 N-benzyl-3-azabicyclo[3.2.1]octane-8α-yl trifluoromethanesulfonate 
• 1147553-19-2 C₂₅H₂₈N₄O₂ 
• 522608-86-2 rac-(1R,5S,8S)-3-benzyl-3-azabicyclo[3.2.1]octan-8-ol 

Relevant academic research and scientific papers

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.

BICYCLIC HETEROCYCLE DERIVATIVES AND METHODS OF USE THEREOF

The present invention relates to Bicyclic Heterocycle Derivatives, compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of GPR119 in a patient.

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.