1422007-49-5

Usage

Uses

Used in Organic Synthesis:
(R)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine is used as a building block in organic synthesis for the creation of more complex molecules. Its unique bicyclic structure and functional groups make it a valuable component in the synthesis of advanced organic compounds.
Used in Pharmaceutical Research:
(R)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine is used as a compound of interest in pharmaceutical research due to its potential biological properties. Its unique structure may offer novel interactions with biological targets, warranting further investigation into its possible therapeutic applications.
Used in Biological Research:
In biological research, (R)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine is used as a subject for exploring its interactions with biological systems. (R)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine's potential to engage with biological targets could lead to new insights in the fields of biochemistry and molecular biology.

Upstream product

• 3459-92-5 DBC 
• 73344-75-9 (±)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine 

Relevant academic research and scientific papers

Exploiting the Biocatalytic Toolbox for the Asymmetric Synthesis of the Heart-Rate Reducing Agent Ivabradine

Several chemoenzymatic routes have been evaluated for the production of the heart-rate reducing agent ivabradine. Lipases and ω-transaminases have been identified as useful biocatalysts for the preparation of key enantiopure precursors. The lipase-catalysed kinetic resolution by alkoxycarbonylation of a racemic primary amine and subsequent chemical reduction of the resulting carbamate provided an N-methylated (S)-amine, one step away from ivabradine. Alternatively, the dynamic kinetic resolution by asymmetric bioamination of an aldehyde precursor enabled, in a four-step sequence, the preparative scale synthesis of enantiopure ivabradine in 50% overall yield. (Figure presented.).

PROCESS FOR THE ENZYMATIC SYNTHESIS OF (7S)-1-(3,4-DIMETHOXYBICYCLO[4.2.0]OCTA-1,3,5-TRIEN-7-YL) N-METHYL METHANAMINE, AND APPLICATION IN THE SYNTHESIS OF IVABRADINE AND SALTS THEREOF

Synthesizing carbamate (IX) comprises performing an enantioselective enzymatic acylation of racemic form of (3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)methanamine (IV) with a lipase (EC 3.1.1.3 in the international classification of enzymes) by carbonate with 1-15 molar equivalents in organic solvents, aqueous solvents, a mixture of organic solvents and/or mixture of organic and aqueous solvents at a concentration of 5-500 g/l per liter of solvents and their mixtures, a E/S ratio of 10/1 to 1/100 and a temperature of 25-40[deg] C. Synthesizing carbamate of formula (IX) comprises performing an enantioselective enzymatic acylation of racemic form of (3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)methanamine of formula (IV) with a lipase (EC 3.1.1.3 in the international classification of enzymes) by carbonate of formula (R1O-(CO)-OR1) with 1-15 molar equivalents in organic solvents, aqueous solvents, a mixture of organic solvents and/or mixture of organic and aqueous solvents at a concentration of 5-500 g/l per liter of solvents and their mixtures, a E/S ratio of 10/1 to 1/100 and a temperature of 25-40[deg] C. R1 : linear or branched 1-6C-alkyl, allyl or benzyl. An independent claim is included for synthesis of (7S)-1-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-yl) N-methyl methanamine of formula (I) comprising performing enzymatic acylation of (IV) to obtain (IX), and performing reduction step using a reducing agent consisting of lithium tetrahydridoaluminate and sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) to obtain (I). ACTIVITY : Cardiant; Vasotropic; Antianginal; Antiarrhythmic. MECHANISM OF ACTION : None given.