89381-13-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino cyclopentanol is used as a key building block for the synthesis of drugs and pharmaceutical intermediates, contributing to the development of new medications and improving existing ones.
Used in Chemical Research and Development:
In the realm of chemical research and development, 2-Amino cyclopentanol is utilized as a crucial starting material for the synthesis of a variety of organic compounds, facilitating advancements in chemical synthesis techniques and the creation of novel chemical entities.
Used as a Chiral Auxiliary:
2-Amino cyclopentanol is employed as a chiral auxiliary in asymmetric synthesis reactions, playing a critical role in enhancing the selectivity and yield of enantioselective syntheses, which is essential for producing pharmaceuticals with desired stereochemistry.

InChI:InChI=1/C5H11NO/c6-4-2-1-3-5(4)7/h4-5,7H,1-3,6H2/t4-,5+/m1/s1

Upstream product

• 221110-46-9 1-azido-2-(trimethylsilyloxy)cyclopentane 
• 672310-36-0 (R,R)-2-N-benzyloxycarbonylaminocyclopentanol 
• 181657-56-7 (1S,2S)-2-(benzyloxy)cyclopentanamine 
• 142-29-0 cyclopentene 
• 33092-86-3 trans-2-aminocyclopentanol 
• 16326-97-9 1,3-dihydroxycyclopentane 
• 285-67-6 Cyclopentene oxide 
• 68327-00-4 (+/-)-trans-2-(N-Benzylamino)cyclopentanol 
• 1033605-25-2 (1S,2S)-trans-2-(N-benzyl)amino-1-cyclopentanol 
• 125356-51-6 (1S,2S)-trans-2-azidocyclopentanol 
• 198422-71-8 benzyl (1S,2S)-trans-N-(2-hydroxycyclopentyl)carbamate 
• 211245-64-6 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde 
• 211245-63-5 [4-cyclopentylamino-2-(methylsulfanyl)pyrimidine-5-yl]methanol 
• 1003-03-8 Cyclopentamine 

Downstream Products

• 68327-04-8 (1S,2S)-2-aminocyclopentanol hydrochloride 
• 137328-52-0 (S,S)-N-(2-hydroxycyclopentyl)-1-isopropyl-6-methylergoline-8-carboxamide 
• 1438288-58-4 1-(3-chlorophenethyl)-3-((1S,2S)-2-hydroxycyclopentyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 454170-16-2 (1R,2R)-trans-2-(tertbutoxycarbonylamino)cyclopentanol 
• 527376-39-2 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycylclopentyl]-1H-imidazole-4-carboxamide 
• 18721-49-8 2-phenyl-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 120-92-3 cyclopentanone 
• 1330069-67-4 trans-N-(2-hydroxycyclopentyl)carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS

Heterocyclic compounds as CDK4 or CDK6 or other CDK inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase

Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.

A practical method for the synthesis of highly enantioenriched trans -1,2-amino alcohols

A highly enantioselective addition of phenyl carbamate to meso-epoxides has been developed to efficiently generate protected trans-1,2-amino alcohols. This transformation is promoted by an oligomeric (salen)Co-OTf catalyst and has been used to prepare two useful 2-aminocycloalkanol hydrochlorides in enantiopure form on a multigram scale from commercially available starting materials.

Direct amination of bio-alcohols using ammonia

A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.

HEPATITIS B ANTIVIRAL AGENTS

The present invention includes a method of inhibiting, suppressing or preventing HBV infection in an individual in need thereof, comprising administering to the individual a therapeutically effective amount of at least one compound of the invention.

Cyclic trans-β-amino alcohols: Preparation and enzymatic kinetic resolution

Enantioenriched cyclic β-amino alcohols, trans-2-aminocyclohexanols (ee, >99%), trans-2-aminocyclopentanols (ee, >99%), trans-1-amino-2- indanols (ee, >99%) and trans-2-amino-1-indanols (ee, ～98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution.

Design and synthesis of a candidate α-human thrombin irreversible inhibitor containing a hydrophobic carborane pharmacophore

α-Human thrombin is a potent platelet agonist involved in the blood coagulation cascade and is an attractive target for an anticoagulant agent due to its involvement in several debilitating diseases. In this contribution we present attempts to develop a new architecture for size-selective serine protease inhibitors that utilize a fully methylated icosahedral p-carborane as a dominating hydrophobic pharmacophore. Using a computational docking program, flexX, a carborane-containing inhibitor was designed and synthesized. Computationally, this compound displayed the ability to provide ligand-protein binding interactions throughout the thrombin's main active site (S1-S3), while positioning an acylating group for facile irreversible attack at the Ser 195 hydroxyl group. Georg Thieme Verlag Stuttgart.

Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis

A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.

Process for the production of optically active amino alcohols

The disclosure describes a process for the preparation of cyclic optically active amino alcohols of formula (I) by reacting an optically active hydroxycarboxylate of formula (IV) with hydrazine to form an optically active hydroxycarboxylic hydrazide compo

Novel compounds

The invention provides novel 1,2,3-triazolo[4,5-d]pyrimidine compounds, their use as medicaments, compositions containing them and processes for their preparation.