40525-77-7

Usage

Uses

Used in Pharmaceutical Research:
3-Amino-cyclohexanol is used as a key intermediate in the synthesis of various pharmaceuticals for its potential role in developing new drugs and therapeutic agents. Its unique structure allows for the creation of a broad range of biologically active compounds, contributing to the advancement of medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Amino-cyclohexanol is used as a building block for the production of chiral ligands and catalysts. Its cyclic structure with both hydroxyl and amino functional groups makes it a versatile component in the synthesis of complex organic molecules.
Used in the Synthesis of Pharmaceutical Intermediates:
3-Amino-cyclohexanol is utilized as a starting material for the synthesis of pharmaceutical intermediates, which are essential precursors in the production of various medications. Its presence in these intermediates can influence the effectiveness and properties of the final drug products.

Upstream product

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

Downstream Products

• 13941-94-1 (rac)-cis-1-(3-hydroxycyclohexyl)benzamide 
• 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 
• 750649-39-9 ((1S,3R)-3-hydroxycyclohexyl)carbamic acid benzyl ester 
• 750649-39-9 ((1R,3S)-3-hydroxycyclohexyl)carbamic acid benzyl ester 
• 750649-39-9 (+/-)-cis-(3-hydroxycyclohexyl)carbamic acid benzyl ester 
• 15676-77-4 cis-3-Tritylamino-cyclohexanol 

Relevant academic research and scientific papers

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.

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.

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.