291775-53-6

Usage

Uses

Used in Pharmaceutical Industry:
(3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
(3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid is used as a key component in the synthesis of complex organic molecules. Its specific stereochemistry and functional groups allow for selective reactions and the formation of a wide range of target molecules.
Used in Hydrogenation of Unfunctionalized Olefins:
(3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid is used as a catalyst or reagent in the hydrogenation of unfunctionalized olefins. This process involves the addition of hydrogen to an olefin, converting it into a saturated hydrocarbon. The use of (3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid in hydrogenation reactions can improve the efficiency and selectivity of the process, leading to the production of desired products with fewer side reactions.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 204327-17-3 (1S,3R,4R)-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester 
• 88260-08-6 2-azabicyclo[2.2.1.]heptane-3-carboxylic acid,ethyl ester 
• 171754-03-3 (1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-3-carboxylic acid 

Downstream Products

• 291775-65-0 (1S,3R,4R)-N-tert-butoxycarbonyl-3-[N-((2S)-2-methoxymethyl)pyrrolidinyl]carbonyl-2-azabicyclo[2.2.1]heptane 
• 385808-49-1 3-[[[3-(Trifluoromethyl)phenyl]amino]carbonyl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester 
• 1246090-86-7 (1S,3R,4R)-tert-butyl 3-(4-phenylthiazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate 
• 1246090-88-9 2-((1S,3R,4R)-2-azabicyclo[2.2.1]heptan-3-yl)-4-phenylthiazole 
• 215674-22-9 (1S,3R,4R)-3-pyrrolidin-1-ylmethyl-2-azabicyclo[2.2.1]heptane 

Relevant academic research and scientific papers

Design, Synthesis and Biological Evaluation of Neogliptin, a Novel 2-Azabicyclo[2.2.1]heptane-Based Inhibitor of Dipeptidyl Peptidase-4 (DPP-4)

Compounds that contain (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid substituted with bicyclic amino moiety (2-aza-bicyclo[2.2.1]heptane) were designed using molecular modelling methods, synthesised, and found to be potent DPP-4 (dipeptidyl peptidase-4) inhibitors. Compound 12a (IC50 = 16.8 ± 2.2 nM), named neogliptin, is a more potent DPP-4 inhibitor than vildagliptin and sitagliptin. Neogliptin interacts with key DPP-4 residues in the active site and has pharmacophore parameters similar to vildagliptin and sitagliptin. It was found to have a low cardiotoxic effect compared to sitagliptin, and it is superior to vildagliptin in terms of ADME properties. Moreover, compound 12a is stable in aqueous solutions due to its low intramolecular cyclisation potential. These findings suggest that compound 12a has unique properties and can act as a template for further type 2 diabetes mellitus drug development.

Extending the substrate scope of bicyclic p-oxazoline/thiazole ligands for ir-catalyzed hydrogenation of unfunctionalized olefins by introducing a biaryl phosphoroamidite group

This study identifies a series of Ir-bicyclic phosphoroamidite-oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E- and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and ?±,?2-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite-oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane-oxazoline/thiazole ligands, by replacing the N-phosphane group with a p-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite-oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the Ndonor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N-phosphane-oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.

Fused cyclic modulators of nuclear hormone receptor function

Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

Fused cyclic modulators of nuclear hormone receptor function

Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

Allylic alcohols via catalytic asymmetric epoxide rearrangement

Epoxides using chiral lithium amides, but other than for a small subset of meso-epoxides, insufficient reactivity and enantioselectivity hamper the existing methods. Furthermore, the chiral reagents are often required in large excess. This study presents a general and highly enantioselective process that, in addition, is based on catalytic amounts (5 mol %) of enantiopure (1S,3R,4R)-3-(1-pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane and lithium diisopropylamide as the stoichiometric base. The influence of structural modification of the catalyst is studied in terms of activity, enantioselectivity, and aggregation behavior. The utility of the process is demonstrated by its application to a variety of epoxide derivatives (≥94% ee for 11 out of 14 examples), including the formal syntheses of, e.g., a prostaglandin core unit, epibatidine, carbovir, faranal, and lasiol. The system is readily extended to the resolution of racemic epoxides, which allows access to highly enantioenriched epoxides or allylic alcohols, even at conversions near 50%.