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192704-54-4

Basic Information
CAS No.: 192704-54-4
Name: Eplerenone intermediate A1
Article Data: 1
Molecular Structure:
Molecular Structure of 192704-54-4 (Eplerenone intermediate A1)
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
Synthetic route
192569-17-8

11α-hydroxyl canrenone

143-33-9

sodium cyanide

192704-54-4

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
ConditionsYield
With sulfuric acid In ISOPROPYLAMIDE; water at 95℃; for 18.5h;3 g
192569-17-8

11α-hydroxyl canrenone

151-50-8

potassium cyanide

192704-54-4

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
ConditionsYield
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

5'R(5'α),7'β-20'-aminohexadecahydro-11'β-hydroxy-10'α,13'α-dimethyl-3',5-dioxospiro[furan-2(3H),17'α(5'H)-[7,4]metheno(4H)cyclopenta[a]phenanthrene]-5'-carbonitrile

192704-54-4

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
ConditionsYield
With hydrogenchloride In methanol; water at 0 - 80℃; for 7h;36.5 kg
192704-54-4

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

124-41-4

sodium methylate

192704-56-6

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
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%
67-56-1

methanol

192704-54-4

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

124-41-4

sodium methylate

192704-56-6

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
Heating / reflux;77%
With zinc(II) iodide
67-56-1

methanol

192704-54-4

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

124-41-4

sodium methylate

107724-20-9

eplerenone

Conditions
ConditionsYield
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
192704-54-4

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

5β-cyano-11α,17-dihydroxy-3-oxo-17α-pregnane-7α,21-dicarboxylic acid, γ-lactone

Conditions
ConditionsYield
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
192704-54-4

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

865-33-8

potassium methanolate

192704-56-6

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

Conditions
ConditionsYield
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
67-56-1

methanol

192704-54-4

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

7-methyl hydrogen 5β-cyano-11α,17-dihydroxy-3-oxo-17α-pregnane-7α,21-dicarboxylate, γ-lactone

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 1.5h;3.6 g
Downstream Products
107724-20-9
192704-56-6
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