6982-42-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-cyclohexanol is used as a building block for the synthesis of various active pharmaceutical ingredients. Its presence in the molecular structure of these ingredients contributes to their therapeutic effects, making it an essential component in the development of new medications.
Used in Organic Synthesis:
3-Amino-cyclohexanol is utilized as a chiral building block in the preparation of enantiomerically pure compounds. Its ability to influence the stereochemistry of synthesized products is crucial for creating compounds with specific biological activities, which is particularly important in the production of high-purity pharmaceuticals and other specialty chemicals.
Used in the Development of New Drugs:
Given its structural features and reactivity, 3-Amino-cyclohexanol is employed in the research and development of novel drug candidates. Its incorporation into drug molecules can lead to the discovery of new therapeutic agents with improved efficacy and selectivity.
Used in the Development of New Materials:
Beyond its pharmaceutical applications, 3-Amino-cyclohexanol also holds potential in the creation of new materials. Its unique chemical properties can be harnessed to develop materials with specialized characteristics for use in various industries, such as coatings, adhesives, or polymers with tailored properties.

Upstream product

• 13941-94-1 (rac)-trans-1-(3-hydroxycyclohexyl)benzamide 
• 5220-49-5 3-amino-cyclohex-2-enone 
• 57376-99-5 (+/-)-N-(cis-3-hydroxy-cyclohexyl)-acetamide 
• 591-27-5 m-Hydroxyaniline 
• 106729-79-7 (+/-)-cis-2-(3-hydroxycyclohexyl)isoindole-1,3-dione 

Downstream Products

• 102653-17-8 (+/-)-trans-1-acetoxy-3-acetylamino-cyclohexane 
• 102653-17-8 cis-3-acetamidocyclohexyl acetate 
• 101265-14-9 (+/-)-N-(cis-3-hydroxy-cyclohexyl)-N'-phenyl-urea 
• 91470-37-0 2-oxa-4-aza-bicyclo[3.3.1]nonan-3-one 
• 1315489-74-7 cis-3-(2-methylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexanol 
• 1315489-73-6 cis-3-(2-methylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexanol 
• 57376-99-5 (+/-)-N-(cis-3-hydroxy-cyclohexyl)-acetamide 
• 102756-76-3 (+/-)-cis-1-(acetyl-benzoyl-amino)-3-benzoyloxy-cyclohexane 
• 101105-28-6 (+/-)-cis-1-acetylamino-3-benzoyloxy-cyclohexane 
• 101354-29-4 (+/-)-N-ethyl-N-(cis-3-hydroxy-cyclohexyl)-N'-phenyl-urea 
• 6982-38-3 (+/-)-cis-3-ethylamino-cyclohexanol 

Relevant academic research and scientific papers

Diastereoisomeric salt formation and enzyme-catalyzed kinetic resolution as complementary methods for the chiral separation of cis-/trans-enantiomers of 3-aminocyclohexanol

This contribution demonstrates the preparative-scale synthesis of (1S,3S)-3-aminocyclohexanol by either enzymatic kinetic resolution of Cbz-protected 3-aminocyclohexanols or direct diastereoisomeric salt formation with (R)-mandelic acid. The salt formation demonstrates how a single enantiomer, (1S,3S)-3-aminocyclohexanol (R)-mandelate, can be effectively isolated from the cis/trans racemic mixture and subsequently converted to the free amine, (1S,3S)-3-aminocyclohexanol, by ion-exchange chromatography. We have also demonstrated how the other three enantiomers of 3-aminocyclohexanol can be prepared by either diastereoisomeric salt formation or enzymatic kinetic resolution.

Resolution of N-protected cis- and trans-3-aminocyclohexanols via lipase-catalyzed enantioselective acylation in organic media

The enzymatic acylation of N-protected cis-and trans-1,3-aminocyclohexanols using lipases in organic solvents is described. By modifying certain reaction parameters such as the solvent, the lipase and the N-protecting group, it is possible to achieve high enantioselectivities and to obtain enantiomerically pure 3-aminocyclohexanols. The influence of the N-protecting group and the conformation of the substrate on the reaction rate was also studied.

Convenient Procedure for the Reduction of β-Enamino Ketones: Synthesis of γ-Amino Alcohols and Tetrahydro-1,3-oxazines

γ-Amino alcohols 3 can be easily synthesized in very good yields by reduction of enaminones 1 with Na in PrOH-tetrahydrofuran.The reaction is fast, easy to perform, inexpensive and the easily accesible starting materials provide a convenient entry to γ-amino alcohols.The relative configuration assignment of the diastereomeric γ-amino alcohols obtained has been established by 1H and 13C NMR studies and unequivocally assigned by their cyclic tetrahydro-1,3-oxazine derivatives 4.