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CAS No.: | 192704-54-4 |
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Name: | Eplerenone intermediate A1 |
Article Data: | 1 |
Molecular Structure: | |
Formula: | C24H29NO5 |
Molecular Weight: | 411.498 |
Synonyms: | 11a-Hydroxycanrenone; |
Density: | 1.36±0.1 g/cm3(Predicted) |
Boiling Point: | 664.7±55.0 °C(Predicted) |
Solubility: | 40mg/L at 20℃ |
PSA: | 104.46000 |
LogP: | 2.57348 |
11α-hydroxyl canrenone
sodium cyanide
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
Conditions | Yield |
---|---|
With sulfuric acid In ISOPROPYLAMIDE; water at 95℃; for 18.5h; | 3 g |
11α-hydroxyl canrenone
potassium cyanide
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
Conditions | Yield |
---|---|
Stage #1: 11α-hydroxyl canrenone; potassium cyanide With sulfuric acid In ISOPROPYLAMIDE; water at 20 - 80℃; for 2 - 3h; Stage #2: With sulfuric acid In ISOPROPYLAMIDE; water at 80 - 102℃; for 2.33h; | 84 g |
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
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 0 - 80℃; for 7h; | 36.5 kg |
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
11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
Conditions | Yield |
---|---|
Stage #1: 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 20h; Heating / reflux; Stage #2: With hydrogenchloride In methanol; water | 78% |
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
11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
Conditions | Yield |
---|---|
Heating / reflux; | 77% |
With zinc(II) iodide |
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 |
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
Conditions | Yield |
---|---|
Stage #1: 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 With sodium acetate In water; acetonitrile for 3h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=4.5 - 5.5; | 4.5 g |
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
potassium methanolate
11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
Conditions | Yield |
---|---|
In methanol for 23.5h; Heating / reflux; | 2.98 g |
Stage #1: 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; potassium methanolate In methanol at 60℃; for 7.5h; Heating / reflux; Stage #2: With hydrogenchloride In methanol; water for 0.25h; | 25 - 27 g |
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
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 1.5h; | 3.6 g |