5913-13-3

Usage

Uses

Used in Pharmaceutical and Chemical Synthesis:
(R)-(-)-1-Cyclohexylethylamine is used as a key intermediate in the preparation of benzylidene(1-cyclohexylethyl)amine by reacting with benzaldehyde. This reaction is crucial for the synthesis of various pharmaceuticals and specialty chemicals that require chiral centers for their biological activity.
Used in Chiral Stationary Phases for Chromatography:
(R)-(-)-1-Cyclohexylethylamine is used to prepare chiral polymethacrylamides, which serve as stationary phases for the liquid-chromatographic resolution of racemic amides. These chiral stationary phases are essential for separating enantiomers, which is critical in the development and manufacturing of chiral drugs.
Used in High Performance Liquid Chromatography (HPLC):
(R)-(-)-1-Cyclohexylethylamine is also used in the preparation of polyamides bound to silica gel for high-performance liquid chromatography. These materials offer pressure stability and are used for the separation and analysis of various compounds in the pharmaceutical, chemical, and environmental industries.
Used in Chiral Calix[4]arene Schiff Base Derivatives:
Furthermore, (R)-(-)-1-Cyclohexylethylamine may be used in the preparation of chiral calix[4]arene Schiff base derivatives. These derivatives possess potential enantioselective recognition ability towards amines, which can be utilized in various applications such as chiral catalysts, sensors, and enantioselective separation techniques.

Purification Methods

Purify it by conversion to the bitartrate salt (m 172o), then decomposing with strong alkali and extracting into Et2O, drying (KOH), filtering, evaporating and distilling. The hydrochloride salt has m 242o (from EtOH/Et2O), [] D -5.0o (c 10 H2O, from (+) amine). The oxalate salt has m 132o (from H2O). The (±)-base has b 176-178o/760mm, and HCl has m 237-238o. [Reihlen et al. Justus Liebigs Ann Chem 532 247 1938, Leithe Chem Ber 65 660 1932, Beilstein 12 III 95.]

InChI:InChI=1/C8H17N/c1-7(9)8-5-3-2-4-6-8/h7-8H,2-6,9H2,1H3

Upstream product

• 540-69-2 ammonium formate 
• 823-76-7 Cyclohexyl methyl ketone 
• 36065-27-7 N-α-phenylethylacetamide 
• 64-17-5 ethanol 
• 6948-01-2 N-formyl-α-methylbenzylamine 
• 16712-16-6 ammonium formate 
• 17430-98-7 [(1S)-1-cyclohexylethyl]amine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 52316-19-5 cyclohexyl methyl ketone oxime 
• 142068-31-3 N'-(1-cyclohexylethylidene)benzohydrazide 
• 4352-49-2 1-cyclohexylethylamine 
• 938076-82-5 (R)-O-methyl-N-hydroxycyclohexylethylamine 
• 618-36-0 rac-methylbenzylamine 
• 134855-88-2 (R)-4-hydroxy-α-methylbenzylamine 

Downstream Products

• 854444-53-4 (1-cyclohexyl-ethyl)-dimethyl-amine 
• 120205-93-8 N-((S)-1-Cyclohexyl-ethyl)-butyramide 
• 120205-93-8 N-((R)-1-Cyclohexyl-ethyl)-butyramide 
• 17430-98-7 [(1S)-1-cyclohexylethyl]amine 
• 823-76-7 Cyclohexyl methyl ketone 
• 1100754-04-8 N-(((S)-1-cyclohexylethylcarbamoyl)methyl)octanamide 
• 1190851-42-3 C₁₈H₃₄N₂O₂ 
• 933065-34-0 N-((R)-1-(cyclohexyl)ethyl)acetamide 

Relevant academic research and scientific papers

Sequential Chiral Induction and Regulator-Assisted Chiral Memory of Pillar[5]arenes

Chirality transfer is widely observed in life processes, and many artificial chiral transfer systems have been developed. In these systems, chiral information is transferred from chiral inducers to chiral acceptors by a direct chiral induction process and a direct chiral memorization process. We have developed ternary nondirect chiral transfer systems based on pillar[5]arenes, in which a third factor was introduced as a regulator. The planar chirality of an acceptor was induced and memorized by a chiral inducer with precise control by a regulator. In the chiral induction period, the feed sequence of the chiral inducer and regulator affected the chiral induction behavior of the chiral acceptor. The chiral memory ability of the acceptor was substantially improved by the combined action of the chiral inducer and regulator.

Chemoselective and Tandem Reduction of Arenes Using a Metal–Organic Framework-Supported Single-Site Cobalt Catalyst

The development of heterogeneous, chemoselective, and tandem catalytic systems using abundant metals is vital for the sustainable synthesis of fine and commodity chemicals. We report a robust and recyclable single-site cobalt-hydride catalyst based on a porous aluminum metal–organic framework (DUT-5 MOF) for chemoselective hydrogenation of arenes. The DUT-5 node-supported cobalt(II) hydride (DUT-5-CoH) is a versatile solid catalyst for chemoselective hydrogenation of a range of nonpolar and polar arenes, including heteroarenes such as pyridines, quinolines, isoquinolines, indoles, and furans to afford cycloalkanes and saturated heterocycles in excellent yields. DUT-5-CoH exhibited excellent functional group tolerance and could be reusable at least five times without decreased activity. The same MOF-Co catalyst was also efficient for tandem hydrogenation–hydrodeoxygenation of aryl carbonyl compounds, including biomass-derived platform molecules such as furfural and hydroxymethylfurfural to cycloalkanes. In the case of hydrogenation of cumene, our spectroscopic, kinetic, and density functional theory (DFT) studies suggest the insertion of a trisubstituted alkene intermediate into the Co–H bond occurring in the turnover limiting step. Our work highlights the potential of MOF-supported single-site base–metal catalysts for sustainable and environment-friendly industrial production of chemicals and biofuels.

Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation

Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.

Ruthenium Catalyzed Direct Asymmetric Reductive Amination of Simple Aliphatic Ketones Using Ammonium Iodide and Hydrogen

The direct conversion of ketones into chiral primary amines is a key transformation in chemistry. Here, we present a ruthenium catalyzed asymmetric reductive amination (ARA) of purely aliphatic ketones with good yields and moderate enantioselectivity: up to 99 percent yield and 74 percent ee. The strategy involves [Ru(PPh3)3H(CO)Cl] in combination with the ligand (S,S)-f-binaphane as the catalyst, NH4I as the amine source and H2 as the reductant. This is a straightforward and user-friendly process to access industrially relevant chiral aliphatic primary amines. Although the enantioselectivity with this approach is only moderate, to the extent of our knowledge, the maximum ee of 74 percent achieved with this system is the highest reported till now apart from enzyme catalysis for the direct transformation of ketones into chiral aliphatic primary amines.

Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases

Chiral primary amines are important intermediates in the synthesis of pharmaceutical compounds. Fungal reductive aminases (RedAms) are NADPH-dependent dehydrogenases that catalyse reductive amination of a range of ketones with short-chain primary amines supplied in an equimolar ratio to give corresponding secondary amines. Herein we describe structural and biochemical characterisation as well as synthetic applications of two RedAms fromNeosartoryaspp. (NfRedAm andNfisRedAm) that display a distinctive activity amongst fungal RedAms, namely a superior ability to use ammonia as the amine partner. Using these enzymes, we demonstrate the synthesis of a broad range of primary amines, with conversions up to >97% and excellent enantiomeric excess. Temperature dependent studies showed that these homologues also possess greater thermal stability compared to other enzymes within this family. Their synthetic applicability is further demonstrated by the production of several primary and secondary amines with turnover numbers (TN) up to 14 000 as well as continous flow reactions, obtaining chiral amines such as (R)-2-aminohexane in space time yields up to 8.1 g L?1h?1. The remarkable features ofNfRedAmand NfisRedAm highlight their potential for wider synthetic application as well as expanding the biocatalytic toolbox available for chiral amine synthesis.

Titanium(III)-Oxo Clusters in a Metal-Organic Framework Support Single-Site Co(II)-Hydride Catalysts for Arene Hydrogenation

Titania (TiO2) is widely used in the chemical industry as an efficacious catalyst support, benefiting from its unique strong metal-support interaction. Many proposals have been made to rationalize this effect at the macroscopic level, yet the underlying molecular mechanism is not understood due to the presence of multiple catalytic species on the TiO2 surface. This challenge can be addressed with metal-organic frameworks (MOFs) featuring well-defined metal oxo/hydroxo clusters for supporting single-site catalysts. Herein we report that the Ti8(μ2-O)8(μ2-OH)4 node of the Ti-BDC MOF (MIL-125) provides a single-site model of the classical TiO2 support to enable CoII-hydride-catalyzed arene hydrogenation. The catalytic activity of the supported CoII-hydride is strongly dependent on the reduction of the Ti-oxo cluster, definitively proving the pivotal role of TiIII in the performance of the supported catalyst. This work thus provides a molecularly precise model of Ti-oxo clusters for understating the strong metal-support interaction of TiO2-supported heterogeneous catalysts.

O -Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P(O)-NH containing compounds

Over 50 years ago, Jencks and Gilchrist showed that formaldehyde catalyses the hydrolysis of phosphoramidate through electrophilic activation, induced by covalent attachment to its nitrogen atom. Given our interest in the use of aldehydes as catalysts, this work was revisited to identify a superior catalyst, o-phthalaldehyde, which facilitates hydrolyses of various organophosphorus compounds bearing P(O)-NH subunits under mild conditions. Interestingly, chemoselective hydrolysis of the P(O)-N bonds could be accomplished in the presence of P(O)-OR bonds.

Optical activity 1-cyclohexyl ethylamine preparation method

The present invention discloses an optical activity 1-cyclohexyl ethylamine preparation method, which comprises that: in water and under the effect of HBr, N-acetylamino-1-cyclohexyl ethylamine represented by a formula 4 or 4' is subjected to a hydrolysis reaction to correspondingly prepare the optical activity 1-cyclohexyl ethylamine represented by a formula 5 or 5'. The preparation method of the present invention can further comprise that a compound represented by a formula I is subjected to an oximation reaction, a reduction acylation reaction and an asymmetric catalysis reaction to prepare the N-acetylamino-1-cyclohexyl ethylamine represented by the formula 4 or 4'. According to the present invention, the preparation method has characteristics of simple operation, low production cost, high product chemical purity, high product optical purity, high product yield, and green environmental protection. The formulas such as 4, 4', 5 and 5' are defined in the specification.

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Imine Reductase-Catalyzed Intermolecular Reductive Amination of Aldehydes and Ketones

Imine reductases (IREDs) have emerged as promising biocatalysts for the synthesis of chiral amines. In this study, the asymmetric imine reductase-catalyzed intermolecular reductive amination with NADPH as the hydrogen source was investigated. A highly chemo- and stereoselective imine reductase was applied for the reductive amination by using a panel of carbonyls with different amine nucleophiles. Primary and secondary amine products were generated in moderate to high yields with high enantiomeric excess values. The formation of the imine intermediate was studied between carbonyl substrates and methylamine in aqueous solution in the pH range of 4.0 to 9.0 by 1H NMR spectroscopy. We further measured the kinetics of the reductive amination of benzaldehyde with methylamine. This imine reductase-catalyzed approach constitutes a powerful and direct method for the synthesis of valuable amines under mild reaction conditions. IRED all about it: The intermolecular asymmetric reductive amination of carbonyls catalyzed by a stereoselective imine reductase produces chiral amines in high yields with high enantioselectivities. The reaction efficiency is attributed to its remarkable tolerance to high concentrations of amine nucleophiles, high pH values, high chemoselectivity towards imines, and high stereoselectivity of the biocatalyst.