291775-53-6

Basic information

• Product Name: (3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid
• Synonyms: (3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid;(1S,3R,4S)-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid;2-Azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, 2-(1,1-diMethylethyl) ester, (1S,3R,4R)-;(1S,3R,4R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid
• CAS NO: 291775-53-6
• Molecular Formula: C₁₂H₁₉NO₄
• Molecular Weight: 241.29
• Mol File: 291775-53-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 148-153 °C
• Boiling Point: 371.0±25.0 °C(Predicted)
• Appearance: /
• Density: 1.232±0.06 g/cm3(Predicted)
• PKA: 4.05±0.20(Predicted)
• CAS DataBase Reference: (3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid(291775-53-6)
• EPA Substance Registry System: (3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid(291775-53-6)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50
• Safety Statements: 36/37/39-61
• Hazardous Substances Data: 291775-53-6(Hazardous Substances Data)

Usage

Description

(3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid is a complex organic compound with a unique bicyclic structure and a carboxylic acid functional group. It is characterized by its stereochemistry, with the 3-position being in the R-configuration. (3R)-N-Boc-2-azabicyclo[2.2.1]heptane-3-carboxylic acid is often utilized in various chemical reactions and processes due to its specific structural features and reactivity.

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 this compound 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 
• 171754-03-3 (1S,3R,4R)-2-aza-bicyclo-[2.2.1]-heptane-3-carboxylic acid 
• 88260-08-6 2-azabicyclo[2.2.1.]heptane-3-carboxylic acid,ethyl ester 
• 204327-17-3 (1S,3R,4R)-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester 

Downstream Products

• 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 
• 291775-65-0 (1S,3R,4R)-N-tert-butoxycarbonyl-3-[N-((2S)-2-methoxymethyl)pyrrolidinyl]carbonyl-2-azabicyclo[2.2.1]heptane 

Relevant articles and documents

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.

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%.