130931-85-0

Basic information

• Product Name: (1R,4S)-4-AMINO-CYCLOPENT-2-ENECARBOXYLIC ACID HYDROCHLORIDE
• Synonyms: (1R,4S)-4-AMINO-CYCLOPENT-2-ENECARBOXYLIC ACID HYDROCHLORIDE;(+)-(1R,4S)-4-Aminocyclopent-2-enecarboxylic acid(absolute)HCl
• CAS NO: 130931-85-0
• Molecular Formula: C₆H₉NO₂*ClH
• Molecular Weight: 163.6021
• Mol File: 130931-85-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 266.6 °C at 760 mmHg
• Flash Point: 115 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (1R,4S)-4-AMINO-CYCLOPENT-2-ENECARBOXYLIC ACID HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-4-AMINO-CYCLOPENT-2-ENECARBOXYLIC ACID HYDROCHLORIDE(130931-85-0)
• EPA Substance Registry System: (1R,4S)-4-AMINO-CYCLOPENT-2-ENECARBOXYLIC ACID HYDROCHLORIDE(130931-85-0)

Safety Data

• Hazardous Substances Data: 130931-85-0(Hazardous Substances Data)

Usage

General Description

"(1R,4S)-4-Amino-cyclopent-2-enecarboxylic acid hydrochloride" is a scientific chemical compound. This complex-named substance, often used in various forms of laboratory and scientific research, falls under the category of organic compounds. As the name indicates, it is a hydrochloride, meaning its structure contains a hydrogen chloride (HCl) group. Additionally, the "4-Amino" section refers to the presence of an amino group, while "cyclopent-2-enecarboxylic acid" suggests a cyclic structure with a double bond and carboxylic acid functional group. However, specific details about its physical properties, uses, and safety measures may vary and should be referred from proper scientific sources.

Synthetic route

(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8) → (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0)

Conditions	Yield
With hydrogenchloride In water for 2h; Reflux;	90%

(-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate] (200002-41-1) → (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0)

Conditions	Yield
With hydrogenchloride In water for 2h; Reflux;	82%

(1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (151907-80-1) → (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 20℃; for 2h;

racemic N-hydroxymethyl vince lactam → (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 0.5 h / 60 °C / Enzymatic reaction 2: hydrogenchloride; water / 5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 2 h / 60 °C / Enzymatic reaction 2: hydrogenchloride; water / 5 h / Reflux View Scheme

(1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one (157810-20-3) → (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0)

Conditions	Yield
With hydrogenchloride; water for 5h; Reflux;

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one (49805-30-3) → (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: Sonication 2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 0.5 h / 60 °C / Enzymatic reaction 3: hydrogenchloride; water / 5 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: Sonication 2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 2 h / 60 °C / Enzymatic reaction 3: hydrogenchloride; water / 5 h / Reflux View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) + 4-((4-phenyl-5-trifluoromethyl-2-thienyl)methoxy)benzaldehyde (569685-43-4) → (1R,4S)-4-(4-((4-phenyl-5-(trifluoromethyl)thiophene-2-yl)methoxy)benzylamino)cyclopentan-2-encarboxylic acid (1008769-14-9)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 6h;

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (+)-methyl (1R,2S,4R,5S)-2-(tert-butoxycarbonylamino)bicyclo[3.1.0]hexane-4-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester (251326-99-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetyl chloride / 16 h / 80 °C 2: triethylamine / dichloromethane / 3 h / 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (1S,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: acetyl chloride / 16 h / 80 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: sodium methylate / methanol / 1 h / -10 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → methyl (1R,2S,4S,5S)-2-(tert-butoxycarbonylamino)bicyclo[3.1.0]hexane-4-carboxylate

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: sodium methylate / methanol / 1 h / -10 °C 4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (+)-(1R,2S,4R,5S)-2-[[5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylic acid

Conditions

Yield

Multi-step reaction with 8 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C 6.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation 6.2: 1 h / 130 °C / Microwave irradiation 7.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C 8.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (1R,2S,4S,5S)-2-[[5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylic acid

Conditions

Yield

Multi-step reaction with 9 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: sodium methylate / methanol / 1 h / -10 °C 4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C 7.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation 7.2: 1 h / 130 °C / Microwave irradiation 8.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C 9.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (+)-methyl (1R,2S,4R,5S)-2-aminobicyclo[3.1.0]hexane-4-carboxylate

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (+)-methyl (1R,2S,4R,5S)-2-[(2-chloro-5-fluoropyrimidin-4-yl)amino]bicyclo[3.1.0]hexane-4-carboxylate

Conditions	Yield
Multi-step reaction with 5 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (+)-methyl (1R,2S,4R,5S)-2-[[5-fluoro-2-(5-fluoro-1-tetrahydropyran-2-yl-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylate

Conditions

Yield

Multi-step reaction with 6 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C 6.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation 6.2: 1 h / 130 °C / Microwave irradiation View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (+)-(1R,2S,4R,5S)-2-({5-fluoro-2-[5-fluoro-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-yl}amino)bicyclo[3.1.0]hexane-4-carboxylic acid

Conditions

Yield

Multi-step reaction with 7 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C 6.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation 6.2: 1 h / 130 °C / Microwave irradiation 7.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → methyl (1R,2S,4S,5S)-2-aminobicyclo[3.1.0]hexane-4-carboxylate

Conditions	Yield
Multi-step reaction with 5 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: sodium methylate / methanol / 1 h / -10 °C 4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C View Scheme

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: sodium methylate / methanol / 1 h / -10 °C 4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C View Scheme

Conditions

Yield

Multi-step reaction with 7 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: sodium methylate / methanol / 1 h / -10 °C 4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C 7.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation 7.2: 1 h / 130 °C / Microwave irradiation View Scheme

Conditions

Yield

Multi-step reaction with 8 steps 1.1: acetyl chloride / 16 h / 80 °C 2.1: triethylamine / dichloromethane / 3 h / 20 °C 3.1: sodium methylate / methanol / 1 h / -10 °C 4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C 4.2: 2 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C 7.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation 7.2: 1 h / 130 °C / Microwave irradiation 8.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C View Scheme

methanol + (+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride (130931-85-0) → (+)-methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

Conditions	Yield
With acetyl chloride at 80℃; for 16h;

Upstream product

• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 157810-20-3 (1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 200002-41-1 (-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate] 
• 151907-80-1 (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid 

Downstream Products

• 1008769-14-9 (1R,4S)-4-(4-((4-phenyl-5-(trifluoromethyl)thiophene-2-yl)methoxy)benzylamino)cyclopentan-2-encarboxylic acid 
• 251326-99-5 (1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester 

Relevant articles and documents

Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

A very efficient enzymatic two-step cascade reaction was devised (E?>?200) for the resolution of activated γ-lactams (±)-1 and (±)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5?equiv) in the presence of benzylamine (1?equiv) in i-Pr2O at 60?°C. The ring-opened enantiomerically pure γ-amino acids (1S,4R)-6 (ee?=?99%, intermediate of abacavir) and (1S,3R)-8 (ee?=?99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee???96%) were obtained in good yields (?43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6·HCl and (1S,3R)-8·HCl or (1S,4R)-3 and (1R,4S)-4 quantitatively, with ee???96%.

Enzymatic method for the synthesis of blockbuster drug intermediates - Synthesis of five-membered cyclic γ-amino acid and γ-lactam enantiomers

A very efficient enzymatic method was developed for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers, intermediates for drugs with a prominent turnover (e.g., abacavir and carbovir), through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.