79389-37-0

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2S)-2-Methylcyclohexylamine is utilized as a key building block in the synthesis of various pharmaceuticals. Its unique chiral properties allow for the creation of enantiomerically pure compounds, which are essential in developing drugs with targeted therapeutic effects and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical sector, (1R,2S)-2-Methylcyclohexylamine serves as a crucial component in the production of certain pesticides and other agricultural chemicals. Its role in these applications is to provide the necessary structural elements for the development of effective and targeted agrochemicals.
Used in Organic Chemistry Research:
(1R,2S)-2-Methylcyclohexylamine is also employed in the field of organic chemistry research, where it is used to explore the properties and reactions of chiral amines. This research contributes to the broader understanding of stereochemistry and its implications in chemical synthesis and biological activity.

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 22554-27-4 (S)-2-methylcyclohexanone 
• 7003-32-9 2-METHYLCYCLOHEXYLAMINE 
• 113-24-6 sodium pyruvate 
• 15963-37-8 trans-2-methylcyclohexanol 
• 2133-66-6 2-(cis-2-methylcyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 116837-34-4 (αR,1R,2S)-(+)-cis-2-Methyl-N-(1-phenylethyl)cyclohexanamin 
• 352695-16-0 (1R_.E)-N-(2-methylcyclohexylidene)-1-phenylethanamine 

Downstream Products

• 91524-54-8 2-{[(E)-(1R,2S)-2-Methyl-cyclohexylimino]-methyl}-phenol 
• 1473450-28-0 4,6-dimethyl-N-((1R,2S)-2-methylcyclohexyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide 
• 1473450-27-9 1,4,6-trimethyl-N-((1R,2S)-2-methylcyclohexyl)-1H-indole-2-carboxamide 

Relevant academic research and scientific papers

Simultaneous Preparation of (S)-2-Aminobutane and d -Alanine or d -Homoalanine via Biocatalytic Transamination at High Substrate Concentration

(S)-2-Aminobutane, d-alanine, and d-homoalanine are important intermediates for the production of various active pharmaceutical ingredients and food additives. The preparation of these small chiral amine or amino acids with high water solubility still demands searching for efficient methods. In this work, we identified an ω-transaminase (ω-TA) from Sinirhodobacter hungdaonensis (ShdTA) that catalyzed the kinetic resolution of racemic 2-aminobutane at a concentration of 800 mM using pyruvate as the amino acceptor, leading to the simultaneous isolation of enantiopure (S)-2-aminobutane and d-alanine in 46% and 90% yield, respectively. In addition, (S)-2-aminobutane (98% ee) and d-homoalanine (99% ee) were isolated in 45% and 93% yield, respectively, in the kinetic resolution of racemic 2-aminobutane at a concentration of 400 mM coupled with deamination of l-threonine by threonine deaminase. We thus developed a biocatalytic process for the practical synthesis of these valuable small chiral amine and d-amino acids.

Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis

Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.

ω-Transaminases for the amination of functionalised cyclic ketones

The potential of a number of enantiocomplementary ω-transaminases (ω-TAms) in the amination of cyclic ketones has been investigated. After a preliminary screening of several compounds with increasing complexity, different approaches to shift the equilibrium of the reaction to the amine products were studied, and reaction conditions (temperature and pH) optimised. Interestingly, 2-propylamine as an amine donor was tolerated by all five selected ω-TAms, and therefore used in further experiments. Due to the higher conversions observed and interest in chiral amines studies then focused on the amination of α-tetralone and 2-methylcyclohexanone. Both ketones were aminated to give the corresponding amine with at least one of the employed enzymes. Moreover, the amination of 2-methylcyclohexanone was investigated in more detail due to the different stereoselectivities observed with TAms used. The highest yields and stereoselectivities were obtained using the ω-TAm from Chromobacterium violaceum (CV-TAm), producing 2-methylcyclohexylamine with complete stereoselectivity at the (1S)-amine position and up to 24 : 1 selectivity for the cis : trans [(1S,2R) : (1S,2S)] isomer.

INDOLE CARBOXAMIDE DERIVATIVES AND USES THEREOF

A compound of Formula (I) is provided that has been shown to be useful for treating a disease, disorder or syndrome that is mediated by the transportation of essential molecules in the mmpL3 pathway: (I) wherein R1, R2, R3, R4, R5 and R6 are as defined herein.

Highly Enantioselective Hydrogen-Transfer Reductive Amination: Catalytic Asymmetric Synthesis of Primary Amines

Ammonium formate is the hydrogen source in the catalytic asymmetric reductive amination of ketones presented here (Leuckart-Wallach-type reaction). The reaction proceeds smoothly in methanol in the presence of Ir, Rh, and Ru catalysts. Primary amines were obtained as products in good yields with high enantioselectivities after hydrolytic workup when [((R)-tol-binap) RuCl 2] was used as the catalyst (see scheme). R1, R 2=alkyl, aryl.