68327-04-8

Basic information

• Product Name: (1S,2S)-trans-2-Aminocyclopentanol hydrochloride
• Synonyms: TRANS-(1S 2S)-2-AMINOCYCLOPENTANOL HYDRO;(1s,2s)-trans-2-aminocyclopentanol hydrochloride;(1S,2S)-2-aMinocyclopentanol hydrochloride;(1S,2S)-2-aMinocyclopentan-1-ol hydrochloride;(1S,2S)-trans-2-AMinocyclopentanol HCl;trans-(1S,2S)-2-Aminocyclopentanol HCL;(1S,2S)-trans-2-Aminocyclopentanhydrochloride 98%;(1S,2S)-2-amino-1-cyclopentanol
• CAS NO: 68327-04-8
• Molecular Formula: C5H12ClNO
• Molecular Weight: 137.61
• Product Categories: Amino Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 68327-04-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 220.9 °C at 760 mmHg
• Flash Point: 87.4 °C
• Appearance: /
• Vapor Pressure: 0.0229mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (1S,2S)-trans-2-Aminocyclopentanol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-trans-2-Aminocyclopentanol hydrochloride(68327-04-8)
• EPA Substance Registry System: (1S,2S)-trans-2-Aminocyclopentanol hydrochloride(68327-04-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-37
• WGK Germany: 2
• F: 10-21
• TSCA: No
• Hazardous Substances Data: 68327-04-8(Hazardous Substances Data)

Usage

Description

(1S,2S)-trans-2-Aminocyclopentanol hydrochloride is an organic compound with a unique cyclopentanol structure featuring a trans-configuration and an amino group. It is a hydrochloride salt, which contributes to its stability and solubility in various solvents. (1S,2S)-trans-2-Aminocyclopentanol hydrochloride is known for its potential applications in the pharmaceutical and chemical industries due to its versatile chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(1S,2S)-trans-2-Aminocyclopentanol hydrochloride is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly trans-hydroxycyclopentyl carboxamides. These carboxamides have been found to possess significant biological activities, making them valuable in the development of new drugs for treating various diseases.
Used in Chemical Industry:
In the chemical industry, (1S,2S)-trans-2-Aminocyclopentanol hydrochloride can be utilized as a building block for the synthesis of complex organic molecules. Its unique structure and reactivity make it a valuable component in the creation of novel compounds with potential applications in various fields, such as materials science, agrochemistry, and specialty chemicals.
Used in Suzuki Reaction:
(1S,2S)-trans-2-Aminocyclopentanol hydrochloride can also be employed in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds, which are essential in the synthesis of many biologically active molecules and advanced materials. The use of this compound in the Suzuki reaction can lead to the development of new and innovative products with improved properties and applications.

InChI:InChI=1/C5H11NO.ClH/c6-4-2-1-3-5(4)7;/h4-5,7H,1-3,6H2;1H/t4-,5-;/m0./s1

Synthetic route

(1R,2R)-2-acetamidocyclopentanol acetate → (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8)

Conditions	Yield
With hydrogenchloride for 3h; Hydrolysis; Heating;	97%

(1S,2S)-2-(benzyloxy)cyclopentanamine → (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol at 20℃; under 2068.65 Torr; for 24h;	93%

(1S,2S)-2-aminocyclopentanol (930-45-0, 33092-86-3, 33092-90-9, 57070-95-8, 59260-76-3, 68327-03-7, 89381-13-5, 135969-63-0) → (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8)

Conditions	Yield
With hydrogenchloride In diethyl ether; ethanol Yield given;

1-azido-2-(trimethylsilyloxy)cyclopentane (221110-46-9) → (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TFA, 2.) H2 / 2.) PtO2 / 1) MeOH, rt, 30 min; 2) MeOH, rt, 40 h 2: HCl / ethanol; diethyl ether View Scheme

17-(5-fluoropyridin-3-yl)oestra-1,3,5(10),16-tetraene-3-carboxylic acid (1428988-52-6) + 11β-fluoro-17-(5-fluoropyridin-3-yl)-N-(2-sulphamoylethyl)oestra-1,3,5(10),16-tetraene-3-carboxamide → 17-(5-fluoropyridin-3-yl)-N-[(1S,2S)-2-hydroxycyclopentyl]oestra-1,3,5(10),16-tetraene-3-carboxamide + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8)

(1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) + 4-bromo-2,6-difluorobenzonitrile (123843-67-4) → 4-bromo-2-fluoro-6-((1S,2S)-2-hydroxycyclopentylamino)benzonitrile (1073973-68-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 120℃; for 2h;	100%

di-tert-butyl dicarbonate (24424-99-5) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (1S,2S)-trans-2-(tert-butoxycarbonylamino)cyclopentanol (145106-43-0)

Conditions	Yield
With triethylamine In methanol for 22h;	97.76%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 0.75h;	7.21 g
With triethylamine In methanol at 0 - 20℃;	2.87 g
With triethylamine In methanol Inert atmosphere;

acetic anhydride (108-24-7) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (S,S)-trans-2-acetamidocyclopentanol (137254-02-5)

Conditions	Yield
With sodium carbonate In acetone 1) 0 deg C --> rt, 1 h; 2) rt, 2 h;	95%

butyryl chloride (141-75-3) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (1S,2S)-N-(2-hydroxycyclopentyl)butyramide

Conditions	Yield
With sodium carbonate In dichloromethane at 20℃; for 1h;	87%

4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-2,6-difluoro-benzonitrile (1073973-06-4) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)-2-fluoro-6-(trans-4-hydroxycyclohexylamino)benzamide

Conditions	Yield
Stage #1: 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-2,6-difluoro-benzonitrile; (1S,2S)-2-aminocyclopentanol hydrochloride With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 50℃; for 1h; Stage #2: With sodium hydroxide; water; dihydrogen peroxide In methanol; dimethyl sulfoxide at 50℃; for 1h;	85.1%

C22H27Cl2N8O3(1-)*Li(1+) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → C27H37Cl2N9O3

Conditions	Yield
With dmap; HATU In N,N-dimethyl-formamide at 20℃; for 20h;	83%

2,6-dichloro-N4,N8-dimethyl-pyrimido[5,4-d]pyrimidine-4,8-diamine (500860-54-8) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (1S,2S)-2-((6-chloro-4,8-bis(methylamino)pyrimido[5,4-d]pyrimidin-2-yl)amino)cyclopentanol

Conditions	Yield
In butan-1-ol	83%

phthalic anhydride (85-44-9) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → 2-((1S,2S)-2-hydroxycyclopentyl)isoindoline-1,3-dione (223761-82-8)

Conditions	Yield
Stage #1: (1S,2S)-2-aminocyclopentanol hydrochloride With triethylamine In toluene at 20℃; for 0.0833333h; Stage #2: phthalic anhydride for 4h; Reflux;	73.5%

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → ethyl 4-((1S,2S)-2-hydroxycyclopentylamino)-2-(methylthio)-pyrimidine-5-carboxylate (1403863-98-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 60℃; for 15h;	73%

4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-4-oxobut-2-enoic acid (1310875-94-5) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (1S,2S)-4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-N-(2-hydroxycyclopentyl)-4-oxobut-2-enamide (1310876-01-7)

Conditions	Yield
Stage #1: 4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-4-oxobut-2-enoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h; Stage #2: (1S,2S)-2-aminocyclopentanol hydrochloride With sodium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 5℃; for 2h;	66%

4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-4-oxobut-2-enoic acid + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (1S,2S)-4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-4-hydroxy-N-(2-hydroxycyclopentyl)-2-oxobut-3-enamide (1445953-99-0)

Conditions	Yield
Stage #1: 4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-4-oxobut-2-enoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h; Cooling; Stage #2: (1S,2S)-2-aminocyclopentanol hydrochloride With sodium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 5℃; for 2h;	66%

6-((3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yloxy)methyl)nicotinic acid + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → N-((1S,2S)-2-hydroxycyclopentyl)-6-(((3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl)oxy)methyl)nicotinamide

Conditions	Yield
Stage #1: 6-((3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yloxy)methyl)nicotinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (1S,2S)-2-aminocyclopentanol hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	65.8%

(1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) + 2,2-difluoro-3-hydroxydodecanoic acid (821801-03-0) → 2,2-Difluoro-3-hydroxy-dodecanoic acid ((1S,2S)-2-hydroxy-cyclopentyl)-amide (821801-05-2)

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	65%

(1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) + 2-(3-fluorophenyl)acetaldehyde (75321-89-0) → (+/-)-tert-butyl 3-((2'-[tert-butoxycarbonyl(3''-fluorophenethyl)amino]ethyl)(methyl)amino)-4-([6'-(tert-butoxycarbonylamino)-4'-methylpyridin-2'-yl]methyl)-pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: (1S,2S)-2-aminocyclopentanol hydrochloride With triethylamine In 1,2-dichloro-ethane at 20℃; for 0.166667h; Molecular sieves 3 Å; Stage #2: 2-(3-fluorophenyl)acetaldehyde With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Product distribution / selectivity;	62%

methanol (67-56-1) + 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-2,6-difluoro-benzonitrile (1073973-06-4) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)-2-fluoro-6-((1S,2S)-2-hydroxycyclopentylamino)benzamide (1073969-37-5) + 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)-2-((1S,2S)-2-hydroxycyclopentylamino)-6-methoxybenzamide (1073969-71-7)

Conditions

Yield

Stage #1: 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-2,6-difluoro-benzonitrile; (1S,2S)-2-aminocyclopentanol hydrochloride With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 50℃; for 18h; Stage #2: With sodium hydroxide; water; dihydrogen peroxide In dimethyl sulfoxide at 50℃; for 2h; Stage #3: methanol With sodium hydroxide; dihydrogen peroxide In dimethyl sulfoxide at 70℃; for 1h;

A 51% B 8%

3-oxo-2-(pyridin-3-yl)-6-[4-(trifluoromethyl)phenyl]-2,3-dihydropyridazine-4-carboxylic acid + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → N-[(1S,2S)-2-hydroxycyclopentyl]-3-oxo-2-(pyridin-3-yl)-6-[4-(trifluoromethyl)phenyl]-2,3-dihydropyridazine-4-carboxamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;	36%

4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-2,6-difluoro-benzonitrile (1073973-06-4) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)-2-fluoro-6-((1S,2S)-2-hydroxycyclopentylamino)benzamide (1073969-37-5)

Conditions	Yield
Stage #1: 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-2,6-difluoro-benzonitrile; (1S,2S)-2-aminocyclopentanol hydrochloride With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 50℃; Stage #2: With sodium hydroxide; water; dihydrogen peroxide In methanol; dimethyl sulfoxide at 50℃;	28%

6-chloro-3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazine (1414773-00-4) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (1S,2S)-2-{[3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-yl]-oxy}cyclopentanamine (1443499-98-6)

Conditions	Yield
Stage #1: (1S,2S)-2-aminocyclopentanol hydrochloride With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 5℃; for 0.0833333h; Cooling with ice; Stage #2: 6-chloro-3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazine In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;	23%

3-(1-benzofuran-2-yl)-6-chloroimidazo[1,2-b]pyridazine (1414772-61-4) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (1S,2S)-2-{[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino}cyclopentanol (1610454-10-8)

Conditions	Yield
With sodium hydrogencarbonate In butan-1-ol at 150℃; for 72h;	16%

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → N-[(1S,trans)-2-hydroxycyclopentyl]adenosine 2',3',5'-tri-O-acetate

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol at 82℃; for 4h; Substitution;

(1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) + 6-chloro-[8-14C]purineriboside 2',3',5'-tri-O-acetate → N-[(1S,trans)-2-hydroxycyclopentyl]-[8-14C]adenosine 2',3',5'-tri-O-acetate

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol at 82℃; for 4h; Substitution;

chloroform (67-66-3) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) + phosphorus (V)-chloride → (-)-cis-2-chloro-cyclopentylamine

phthalic anhydride (85-44-9) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → 2-(2S-Hydroxy-(S)-cyclopentyl)-isoindole-1,3-dione

Conditions	Yield
In methanol; sodium methylate; ethyl acetate; toluene

(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (676559-69-6) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → (2S,5R)-5-ethynyl-1-{N-((2S)-2-hydroxycyclopentyl)glycyl}pyrrolidine-2-carbonitrile

Conditions	Yield
With triethylamine In acetonitrile
With triethylamine In acetonitrile

(2,6-difluoro-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)benzonitrile) (1073973-05-3) + (1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) → 2-fluoro-6-((1S,2S)-2-hydroxy-cyclopentylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile (1073974-02-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 60℃; for 4h;

(1S,2S)-2-aminocyclopentanol hydrochloride (68327-04-8) + 4-((triisopropylsilyloxy)methyl)benzaldehyde (313279-15-1) → C22H37NO2Si

Conditions	Yield
With magnesium sulfate; triethylamine In dichloromethane at 20℃; for 3h;

Upstream product

• 930-45-0 (1S,2S)-2-aminocyclopentanol 
• 259233-68-6 (1R,2R)-2-acetamidocyclopentanol acetate 
• 221110-46-9 1-azido-2-(trimethylsilyloxy)cyclopentane 
• 181657-56-7 (1S,2S)-2-(benzyloxy)cyclopentanamine 
• 1428988-52-6 17-(5-fluoropyridin-3-yl)oestra-1,3,5⁽¹⁰⁾,16-tetraene-3-carboxylic acid 
• 16936-83-7 (+/-)-2-(4-nitro-phenyl)-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopentoxazole 
• 33092-86-3 trans-2-aminocyclopentanol 
• 33092-88-5 (+/-)-4-nitro-benzoic acid-(trans-2-hydroxy-cyclopentylamide) 

Downstream Products

• 137254-02-5 (S,S)-trans-2-acetamidocyclopentanol 
• 1073969-37-5 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)-2-fluoro-6-((1S,2S)-2-hydroxycyclopentylamino)benzamide 
• 1073973-68-8 4-bromo-2-fluoro-6-((1S,2S)-2-hydroxycyclopentylamino)benzonitrile 
• 1073969-71-7 4-(3-ethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)-2-((1S,2S)-2-hydroxycyclopentylamino)-6-methoxybenzamide 
• 1073974-02-3 2-fluoro-6-((1S,2S)-2-hydroxy-cyclopentylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile 
• 1310876-01-7 (1S,2S)-4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-N-(2-hydroxycyclopentyl)-4-oxobut-2-enamide 
• 145106-43-0 (1S,2S)-trans-2-(tert-butoxycarbonylamino)cyclopentanol 

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