17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester
eplerenone
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; trichloroacetamide; dihydrogen peroxide In dichloromethane at 0 - 15℃; for 24h; pH=9; | 98% |
With trichloroacetamide; dihydrogen peroxide; potassium acetate In dichloromethane at 10 - 15℃; for 0.75h; Temperature; | 91.3% |
With potassium phosphate; trichloroacetamide; dihydrogen peroxide In dichloromethane at 20℃; | 85.3% |
methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone
eplerenone
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; dihydrogen peroxide | 82% |
Multi-step reaction with 2 steps 1: potassium formate; formic acid / acetic anhydride / 100 °C 2: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme |
methanol
4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile
sodium methylate
eplerenone
Conditions | Yield |
---|---|
Stage #1: methanol; 4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile; sodium methylate for 20.25h; Heating / reflux; Stage #2: With hydrogenchloride In methanol; water Heating / reflux; Stage #3: With dipotassium hydrogenphosphate; formic acid; dihydrogen peroxide; potassium formate; acetic anhydride; methanesulfonyl chloride; triethylamine; trichloroacetonitrile more than 3 stages; | 27.1% |
Stage #1: methanol; 4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile; sodium methylate at 67℃; for 16 - 20h; Stage #2: With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 0.75h; Stage #3: With dipotassium hydrogenphosphate; formic acid; dihydrogen peroxide; potassium formate; acetic anhydride; trichloroacetonitrile more than 3 stages; | 7.2 g |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 24h; Heating / reflux; | 20% |
Δ9(11)-canrenone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 82 g / AlEt3 / hexane; tetrahydrofuran / 0.5 h / Heating 2: 6.9 g / DIBAH / 1,2-dimethoxy-ethane; hexane / 2 h / 5 °C 3: 6.6 g / aq. CrO3, H2SO4 / acetone / 0.5 h / 5 °C 4: 2.7 g / CH2Cl2; diethyl ether / 0.17 h 5: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C View Scheme | |
Multi-step reaction with 5 steps 1.1: boron trifluoride diethyl etherate / tetrahydrofuran / -10 °C 2.1: N-Bromosuccinimide; potassium carbonate / tetrahydrofuran; water / 35 °C 3.1: ozone / dichloromethane; isopropyl alcohol / -20 °C 3.2: 20 °C 4.1: potassium hydrogencarbonate / tetrahydrofuran / 10 °C 5.1: dipotassium hydrogenphosphate; 2-chloro-2,2-difluoroacetamide; dihydrogen peroxide / toluene / 55 °C View Scheme |
C23H30O4
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 6.6 g / aq. CrO3, H2SO4 / acetone / 0.5 h / 5 °C 2: 2.7 g / CH2Cl2; diethyl ether / 0.17 h 3: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C View Scheme |
17β-hydroxy-7α-cyano-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 6.9 g / DIBAH / 1,2-dimethoxy-ethane; hexane / 2 h / 5 °C 2: 6.6 g / aq. CrO3, H2SO4 / acetone / 0.5 h / 5 °C 3: 2.7 g / CH2Cl2; diethyl ether / 0.17 h 4: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C View Scheme |
17β-hydroxypregna-4,9(11)-dien-3-one-7α,21-dicarboxylic acid γ-lactone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2.7 g / CH2Cl2; diethyl ether / 0.17 h 2: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C View Scheme |
Conditions | Yield |
---|---|
for 23.5h; Heating / reflux; |
17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester
E
eplerenone
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetonitrile In dichloromethane; water at 8 - 10℃; for 23h; | A n/a B 123 mg C n/a D 46.7 mg E 3.16 g |
eplerenone
11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C 1.2: 4 h 2.1: potassium carbonate / 0 - 20 °C 3.1: triethylamine / dichloromethane / 0 °C 4.1: potassium formate; formic acid / acetic anhydride / 100 °C 5.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C 1.2: 4 h 2.1: potassium carbonate / acetone / 0 - 20 °C 3.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 4.1: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere 5.1: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9 View Scheme |
11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C 2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C 2.2: 4 h 3.1: potassium carbonate / 0 - 20 °C 4.1: triethylamine / dichloromethane / 0 °C 5.1: potassium formate; formic acid / acetic anhydride / 100 °C 6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme |
11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 °C 2: potassium formate; formic acid / acetic anhydride / 100 °C 3: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuryl dichloride; 1H-imidazole / tetrahydrofuran / 1.5 h / -10 - 20 °C 2: trichloroacetamide; disodium hydrogenphosphate; dihydrogen peroxide / dichloromethane / 18 h / 15 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere 3: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9 View Scheme |
9α,11α-epoxy-17β-hydroxypregn-4-en-3-one-7α,21-dicarboxylic acid γ-lactone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / 0 - 20 °C 2: triethylamine / dichloromethane / 0 °C 3: potassium formate; formic acid / acetic anhydride / 100 °C 4: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere 4: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9 View Scheme |
11α-hydroxyl canrenone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 °C 2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C 2.2: 4 h 3.1: potassium carbonate / 0 - 20 °C 4.1: triethylamine / dichloromethane / 0 °C 5.1: potassium formate; formic acid / acetic anhydride / 100 °C 6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C 2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C 2.2: 4 h 3.1: potassium carbonate / 0 - 20 °C 4.1: triethylamine / dichloromethane / 0 °C 5.1: potassium formate; formic acid / acetic anhydride / 100 °C 6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C 2.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C 3.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C 3.2: 4 h 4.1: potassium carbonate / 0 - 20 °C 5.1: triethylamine / dichloromethane / 0 °C 6.1: potassium formate; formic acid / acetic anhydride / 100 °C 7.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 - 100 °C 2.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C 2.2: 4 h 3.1: potassium carbonate / acetone / 0 - 20 °C 4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 5.1: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere 6.1: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9 View Scheme |
9(11)-encanrenone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: boron trifluoride diethyl etherate / acetonitrile / 4 h / -25 - -20 °C / Inert atmosphere 2: potassium carbonate; 5,5-dibromohydantoin / tetrahydrofuran; water / 20 °C / Inert atmosphere 3: ozone / -50 °C 4: trichloroacetamide; potassium phosphate; dihydrogen peroxide / dichloromethane / 20 °C View Scheme |
17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; 5,5-dibromohydantoin / tetrahydrofuran; water / 20 °C / Inert atmosphere 2: ozone / -50 °C 3: trichloroacetamide; potassium phosphate; dihydrogen peroxide / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; potassium carbonate / tetrahydrofuran; water / 35 °C 2.1: ozone / dichloromethane; isopropyl alcohol / -20 °C 2.2: 20 °C 3.1: potassium hydrogencarbonate / tetrahydrofuran / 10 °C 4.1: dipotassium hydrogenphosphate; 2-chloro-2,2-difluoroacetamide; dihydrogen peroxide / toluene / 55 °C View Scheme |
eplerenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ozone / dichloromethane; isopropyl alcohol / -20 °C 1.2: 20 °C 2.1: potassium hydrogencarbonate / tetrahydrofuran / 10 °C 3.1: dipotassium hydrogenphosphate; 2-chloro-2,2-difluoroacetamide; dihydrogen peroxide / toluene / 55 °C View Scheme |
eplerenone
Conditions | Yield |
---|---|
Stage #1: eplerenone With sodium hydroxide In water; acetonitrile at 25 - 90℃; for 66.67h; Heating / reflux; Stage #2: With sulfuric acid In water; acetonitrile | 67% |
Multi-step reaction with 2 steps 1: lithium hydroxide / water / 48 h 2: hydrogenchloride / water View Scheme |
eplerenone
Conditions | Yield |
---|---|
With sodium methylate In methanol for 24h; Reflux; | A 49% B 0.55 g |
eplerenone
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; water at 25 - 70℃; for 6h; | 0.55 g |
eplerenone
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water at 70℃; for 0.666667h; |
eplerenone
Conditions | Yield |
---|---|
With sodium methylate In methanol at 50 - 65℃; for 16.5h; Heating / reflux; | 400 mg |
orthoformic acid triethyl ester
eplerenone
Conditions | Yield |
---|---|
Stage #1: orthoformic acid triethyl ester; eplerenone; toluene-4-sulfonic acid In ethanol at 20℃; for 0.5h; Stage #2: With pyridine; sodium acetate In ethanol | 33.8 g |
eplerenone
C47H42O10
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium hydroxide / water / 48 h 2: hydrogenchloride / water 3: dmap; dicyclohexyl-carbodiimide View Scheme |
eplerenone
C23H30O7
Conditions | Yield |
---|---|
With lithium hydroxide In water for 48h; |
1. Introduction of Eplerenone
Eplerenone, with its systematic name of Methyl (4aS,4bR,5aR,6aS,7R,9aS,9bR,10R)-4a,6a-dimethyl-2,5'-dioxo-2,4,4',4a,5',5a,6,6a,8,9,9a,9b,10,11-tetradecahydro-3H,3'H-spiro[cyclopenta[7,8]phenanthro[4b,5-b]oxirene-7,2'-furan]-10-carboxylate, is one kind of white crystalline powder. Its Classification Code are including Aldosterone antagonist; Aldosterone antagonists; Antihypertensive; Hormone Antagonists; Hormones, Hormone Substitutes, and Hormone Antagonists.
2. Properties of Eplerenone
Eplerenone has the following datas: (1)Index of Refraction: 1.587; (2)Molar Refractivity: 106.122 cm3; (3)Molar Volume: 315.658 cm3; (4)Surface Tension: 53.062 dyne/cm; (5)Density: 1.313 g/cm3; (6)Flash Point: 259.474 °C; (7)Enthalpy of Vaporization: 89.051 kJ/mol; (8)Boiling Point: 597.933 °C at 760 mmHg; (9)Vapour Pressure: 0 mmHg at 25 °C; (10)Melting Point: 241-243 °C.
3. Use of Eplerenone
Eplerenone is an aldosterone antagonist used as an adjunct in the management of chronic heart failure. Eplerenone is used alone or in combination with other medications to treat high blood pressure.Common adverse drug reactions associated with the use of Eplerenone include: hyperkalaemia, hypotension, dizziness, altered renal function, and increased creatinine concentration.
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