32635-39-5

Basic information

• Product Name: Cyclopentanol, 2-(1-pyrrolidinyl)-, trans- (8CI,9CI)
• Synonyms: Cyclopentanol, 2-(1-pyrrolidinyl)-, trans- (8CI,9CI);(1R,2R)-2-pyrrolidin-1-ylcyclopentanol(SALTDATA: FREE);trans-2-Pyrrolidin-1-ylcyclopentanol
• CAS NO: 32635-39-5
• Molecular Formula: C₉H₁₇NO
• Molecular Weight: 155.23738
• Product Categories: CYCLOPENTANE
• Mol File: 32635-39-5.mol

Chemical Properties

• Melting Point: 34.5-35.5 °C
• Boiling Point: 100-104 °C(Press: 1.2 Torr)
• Appearance: /
• Density: 1.115±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.94±0.40(Predicted)
• CAS DataBase Reference: Cyclopentanol, 2-(1-pyrrolidinyl)-, trans- (8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanol, 2-(1-pyrrolidinyl)-, trans- (8CI,9CI)(32635-39-5)
• EPA Substance Registry System: Cyclopentanol, 2-(1-pyrrolidinyl)-, trans- (8CI,9CI)(32635-39-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 32635-39-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cyclopentanol, 2-(1-pyrrolidinyl)-, trans(8CI,9CI) is used as a chemical intermediate for the synthesis of various drugs and chemicals. Its unique structure and properties make it a valuable component in the development of new therapeutic agents and medicinal products.
In the Laboratory and Industrial Settings:
Cyclopentanol, 2-(1-pyrrolidinyl)-, trans(8CI,9CI) is used in research and development for the creation of new pharmaceutical compounds. It is important to handle this chemical with care and follow safety precautions when working with it in a laboratory or industrial setting to ensure the safety of personnel and the integrity of the chemical process.

Upstream product

• 123-75-1 pyrrolidine 
• 285-67-6 Cyclopentene oxide 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 109433-60-5 dimethyl trans-(2-morpholinocyclopentyl)boronate 
• 285-67-6 (1S,5R)-6-Oxa-bicyclo[3.1.0]hexane 

Downstream Products

• 67440-77-1 (3,4-Dichloro-phenyl)-((1S,2S)-2-pyrrolidin-1-yl-cyclopentyl)-amine 
• 67450-59-3 N-(3,4-Dichloro-phenyl)-N-((1R,2R)-2-pyrrolidin-1-yl-cyclopentyl)-propionamide 

Relevant articles and documents

Optimisation of the Anti-Trypanosoma brucei Activity of the Opioid Agonist U50488

Screening of the Sigma-Aldrich Library of Pharmacologically Active Compounds (LOPAC) against cultured Trypanosoma brucei, the causative agent of African sleeping sickness, resulted in the identification of a number of compounds with selective antiproliferative activity over mammalian cells. These included (+)-(1R,2R)-U50488, a weak opioid agonist with an EC50 value of 59nM as determined in our T.brucei invitro assay reported previously. This paper describes the modification of key structural elements of U50488 to investigate structure-activity relationships (SAR) and to optimise the antiproliferative activity and pharmacokinetic properties of this compound.

Aminolysis of epoxides using iridium trichloride as an efficient catalyst

Iridium trichloride catalyzes the ring opening of epoxides by aryl, heterocyclic, or aliphatic amines under mild conditions. The reactions proceed at room temperature to afford the corresponding b-amino alcohols in excellent yields. In general, the aminolysis of cyclopentene oxide is faster than that of cyclohexene oxide in the presence of iridium trichloride as a catalyst. Georg Thieme Verlag Stuttgart.

Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines

In the presence of a catalytic amount of Bi(OTf)3·4H2O and under microwave irradiation, neat mixtures of epoxides and amines afforded smoothly the corresponding 2-amino alcohols. A wide variety of aliphatic amines were reacted with cycloalkene oxide, styrene oxide, and stilbene oxide. The reaction proceeded rapidly and afforded the 2-amino alcohols in high up to quantitative yields. All products could be obtained without aqueous work-up by simple filtration.

Diamino benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors: 3. Enhancing activity by imposing conformational restriction in the C-4'' side chain

The preparation and biological evaluation of a series of benzo[b]thiophene diamine thrombin inhibitors possessing conformationally restricted C-4'' linkers are reported. Compared to the parent compounds 1a/b, the unsaturated derivatives 3a/b exhibited a m

Boranes in Synthesis. 5. The Hydroboration of Enamines with Mono- and Dialkylboranes. Asymmetric Synthesis of β-Amino Alcohols of Moderate Enantiomeric Purity from Aldehyde Enamines

The hydroboration of both acyclic and cyclic aldehyde and ketone enamines with such representative mono- and dialkylboranes as thexylborane and dicyclohexylborane, followed by an oxidative workup, yields the corresponding β-amino alcohols in good to excellent isolated yields.The hydroboration of ketone and aldehyde enamines with the asymmetric hydroboration reagents monoisopinocampheylborane (dIpeBH2) and diisopinocampheylborane (dIpc2BH) was also investigated. dIpc2BH is highly effective for the asymmetric hydroboration of acyclic aldehyde enamines, such as 1-(4-morpholino)-3-phenyl-1-propene and 1-(1-pyrrolidino)-1-octene.Oxidation of the intermediate trialkylborane furnishes the corresponding β-amino alcohols in 50-86percent ee.The stereogenic center of the carbinol carbon is consistently enriched in the R-enantiomer when dIpc2BH prepared from (+)-α-pinene is used as the hydroboration reagent.The enantiomeric excesses of the β-amino alcohols synthesized in this study were determined by HPLC using a chiral stationary phase.The absolute configuration of some of the β-amino alcohols synthesized in this study were determined by chiral HPLC comparison with authentic β-amino alcohols prepared from chiral epoxides of known absolute configuration.

Hydroboration. 81. Synthesis of 2-(Dialkylamino)boronic Esters and Acids via Hydroboration of Enamines. A Convenient Preparation of β-Dialkylamino Alcohols

Hydroboration of representative enamines with 1 equiv of borane-dimethyl sulfide (BMS) in tetrahydrofuran affords as the major product the corresponding boranes, which are charakterized by B NMR spectroscopy.These intermediates on methanolysis give the corresponding boronic acids in essentially quantitative yields.The boronic acids thus obtained can be reestrified with 1,3-propanediol to give the corresponding 2--1,3,2-dioxaborinanes.Consequently, it is now possible to prepare dialkyloamino-substituted organoborane compounds with the potential to be elaborated to a wide variety of functionalized tiralkylamines.Alkaline hydrogen peroxide oxidation of these organoborane intermediates affords the corresponding β-dialkyloamino alcohols.The hydroboration of enamines, methanolysis of the intermediate borane derivatives, and oxidation of the boronate esters is accompanied by side reactions such as elimination and protonolysis.The magnitude of these side reactions varies considerably with the structures of the anamines.However, moderate to excellent yields of the desired organoboron compounds can frequently be achieved.The use of trimethylamine N-oxide dihydrate for the oxidation of the 2-(dialkylamino)boronate esters greatly suppresses the side reactions and vastly improves the yields of the β-dialkylamino alcohols.

FACILE AMINOLYSIS OF EPOXIDES WITH DIETHYLALUMINUM AMIDES

Treatment of an epoxide with a diethylaluminum amide in dichloromethane at room temperature affords the corresponding β-amino alcohol in good yield.

A new nontricyclic antidepressant agent. Synthesis and activity of N-[trans-2-(dimethylamino)cyclopentyl]-N-(3,4-dichlorphenyl)propanamide and related compounds

A series of new nontricyclic antidepressant compounds was synthesized. A representative of this class is shown. Five structural parameters were investigated: ring size, cis/trans stereochemistry, amide substitution, aromatic substitution, and amine substi