16934-77-3

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2R,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXANAMINE is used as a building block in the synthesis of pharmaceuticals due to its unique stereochemistry and chemical properties. It is instrumental in the creation of various medicinal compounds, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Industry:
In the chemical industry, (1R,2R,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXANAMINE serves as a chiral intermediate in asymmetric synthesis. Its specific stereochemistry makes it a valuable component in the production of enantiomerically pure compounds, which are essential in various chemical processes and applications.
Used in Asymmetric Synthesis:
(1R,2R,5R)-2-ISOPROPYL-5-METHYLCYCLOHEXANAMINE is used as a chiral intermediate for asymmetric synthesis, leveraging its stereochemical properties to facilitate the production of enantiomerically pure compounds. This is crucial in creating compounds with specific biological activities and reducing unwanted side effects in pharmaceutical applications.

Upstream product

• 10458-14-7 (2R,5S)-menthone 
• 540-69-2 ammonium formate 
• 799292-75-4 (+)-isomenthone oxime 
• 2385-77-5 (R)-Citronellal 
• 65620-72-6 (1R,5S)-menthone oxime 
• 64-17-5 ethanol 
• 1198-91-0 (+/-)-isomenthone oxime 
• 898543-45-8 2‐azido‐1‐isopropyl‐4‐methylcyclohexane 
• 490-99-3 DL-neomenthol 
• 2216-51-5 (-)-menthol 

Downstream Products

• 500-00-5 3-p-menthene 
• 883-86-3 N-((1R)-neoisomenthyl)-propionamide 
• 885-78-9 N-((1R)-neoisomenthyl)-isobutyramide 
• 885-79-0 N-((1R)-neoisomenthyl)-butyramide 
• 52209-29-7 dimethyl-((1R)-neoisomenthyl)-amine 
• 16508-42-2 trimethyl-((1R)-neoisomenthyl)-ammonium; iodide 
• 7231-40-5 (+)-(1R,3S,4S)-neomenthylamine 
• 51743-63-6 (+)-neomenthylamine 
• 21411-81-4 2-isopropyl-5-methyl-cyclohexylamine 
• 20706-69-8 (1S,3S,4R)-menthylamine 
• 2216-54-8 L-menthylamine 
• 20108-91-2 C-chloro-N-((1R)-neoisomenthyl)-acetamide 

Relevant academic research and scientific papers

Efficient resolution of menthylamine with inexpensive (r,r)-tartaric acid by dielectrically controlled resolution (DCR)

A practical procedure for the resolution of menthylamine 2 with (R,R)-tartaric acid [(R,R)-3] as resolving agent is presented. Variation of the solvent system allows both enantiomers of 2 to be selectively crystallized. Performing the resolution in methanol containing 6 % water leads to (-)-2·(R,R)-3·MeOH. The other, less-soluble diastereomeric salt is obtained by applying a solvent system consisting of methanol with 19 % water with a yield of 14 %. Subsequent basic workup with aqueous sodium hydroxide gave the free menthylamine compounds. Further workup of the mother liquors and an additional recrystallization step allowed the (-)-2·(R,R)-3·MeOH salt to be obtained in an overall yield of 22 %; the other salt (+)-2·(R,R)-3·MeOH·H2O was obtained in 23 % yield. This is another important example of the dielectrically controlled resolution of an interesting amine by using inexpensive (R,R)-tartaric acid as resolving agent. With the same inexpensive resolving agent, (R,R)-tartaric acid, both antipodes of menthylamine can be selectively crystallized as diastereomeric salts. The concentration of water determines which salt is formed. In a few simple resolution steps, good yields and high enantiomeric excess can be achieved. Copyright

Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime

In the current work gold nanoparticles supported on oxides (MgO, Al2O3, ZrO2, TiO2) were used for menthylamine synthesis via menthone oxime hydrogenation. An increase of the gold nanoparticles size and application of metal oxides with a strong basic character such as magnesia favored deoximation to menthone. Au/Al2O3 catalyst with the gold nanoparticles size of 2.0 nm afforded high catalytic activity and selectivity to menthylamine. The reaction kinetics including stereoselectivity to the reaction products and recyclability of the catalyst was studied using Au/Al2O3 in the temperature range 90?110 °C under hydrogen pressure of 5.5–7.5 bar. The catalytic behavior was influenced by the solvent nature, with higher selectivity to desired amine achieved using methanol. The reaction rate was pressure independent, while has first order with respect to menthone oxime concentration. Stereoselectivity to menthylamines and menthones was independent on the reaction temperature and the hydrogen pressure.

Asymmetric hydroamination catalyzed by in situ generated chiral amidate and ureate complexes of zirconium - Probing the role of the tether in ligand design

Simple chiral proligands have been synthesized from inexpensive chiral starting materials. These amidate and ureate ligands support zirconium complexes that successfully catalyze intramolecular hydroamination with up to 26% ee. Several elements necessary for successful ligand design are highlighted and discussed. In particular, the strict control of metal geometry through multidentate tethered ligands is determined to be an essential aspect of future ligand development.

Practical synthesis of optically pure menthylamines starting from racemic neomenthol

A reliable and scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines.

Biomimetic Polyene Cyclizations. Asymmetric Induction during the Acid-Catalyzed Cyclization of Chiral Imines

This paper reports the details of a basic study showing that an imino function is suitable to initiate acid-catalyzed cyclizations of polyenes, affording high yields of cyclized products.The additional advantage of such a function is to introduce very easily a chirality on the polyene skeleton by the way of a chiral group linked to nitrogen.The extent of asymmetric induction by a chiral phenethyl group on nitrogen is from 36percent to 65percent, according to the monocyclic or bicyclic nature of the substrate.