(2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate

Base Information

• Chemical Name: (2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate
• CAS No.: 95716-70-4
• Molecular Formula: C24H30O5
• Molecular Weight: 398.499
• Hs Code.: 2942000000
• European Community (EC) Number: 619-164-5
• UNII: J8799R5TMR
• Nikkaji Number: J2.315.579F
• Mol file: 95716-70-4.mol

Synonyms:95716-70-4;(2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate;J8799R5TMR;Eplerenone impurity C [EP];UNII-J8799R5TMR;(7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylic acid g-lactone methyl ester;Methyl (7R,8R,10S,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-carboxylate;C24H30O5;7alpha-(Methoxycarbonyl)-3-oxo-17alpha-pregna-4,9(11)-diene-21,17-carbolactone;Pregna-4,9(11)-diene-7,21-dicarboxylic acid, 17-hydroxy-3-oxo-, gamma-lactone, 7-methyl ester, (7alpha,17alpha)-;delta 9,11-Eplerenone;SCHEMBL14085016;(7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester;AKOS015920137;DS-1266;methyl (2R,2'S,9'R,10'R,11'S,15'S)-2',15'-dimethyl-5,5'-dioxospiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-1'(17'),6'-diene-9'-carboxylate;EPLERENONE IMPURITY C [EP IMPURITY];CS-0158286;Q-102808;METHYL3-([3-(CHLOROMETHYL)BENZOYL]AMINO)THIOPHENE-2-CARBOXYLATE;(17R)-3-Oxo-7alpha-(methoxycarbonyl)-17-hydroxypregna-4,9(11)-diene-21-carboxylic acid 21,17-lactone;(7alpha,17alpha)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester;7.ALPHA.-(METHOXYCARBONYL)-3-OXO-17.ALPHA.-PREGNA-4,9(11)-DIENE-21,17-CARBOLACTONE;methyl (1R,3aS,3bR,4R,9aS,11aS)-9a,11a-dimethyl-5',7-dioxo-2,3,3a,3b,4,5,7,8,9,9a,11,11a-dodecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-4-carboxylate;Pregna-4,9(11)-diene-7,21-carboxylic acid,17-hydroxy-3-oxo-g-lactone, methyl ester(7a,17a);PREGNA-4,9(11)-DIENE-7,21-DICARBOXYLIC ACID, 17-HYDROXY-3-OXO-, .GAMMA.-LACTONE, 7-METHYL ESTER, (7.ALPHA.,17.ALPHA.)-;Pregna-4,9(11)-diene-7,21-dicarboxylic acid, 17-hydroxy-3-oxo-,g-lactone, methyl ester, (7a,17a)-

Chemical Property of (2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate

Chemical Property:

• Refractive Index: 1.576
• Boiling Point: 580.2 °C at 760 mmHg
• Flash Point: 251.7 °C
• PSA: 69.67000
• Density: 1.24 g/cm³
• LogP: 3.91330
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetone (Slightly), Chloroform (Slightly), Dichloromethane (Slightly), Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 398.20932405
• Heavy Atom Count: 29
• Complexity: 869

Purity/Quality:

99% ^*data from raw suppliers

Δ9,11-Eplerenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CC(C3C2=CCC4(C3CCC45CCC(=O)O5)C)C(=O)OC
• Isomeric SMILES: C[C@]12CCC(=O)C=C1C[C@H]([C@@H]3C2=CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C)C(=O)OC
• Uses: Intermediate in the preparation of Eplerenone and its derivatives. Δ9,11-Eplerenone (Eplerenone EP Impurity C) is an intermediate in the preparation of Eplerenone and its derivatives.

Technology Process of (2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate

There total 31 articles about (2'R,7R,8R,10S,13S,14S)-Methyl 10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,10,12,13,14,15,16-tetradecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.9%

17α-pregna-4-ene-7α,21-dicarboxylic acid-11α,17β-dihydroxy-3-oxo-γ-lactone-7-methyl ester → 17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester (95716-70-4)

Guidance literature:

With phosphorus pentachloride; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 ℃; for 0.166667h; Reagent/catalyst; Temperature;

Reference yield: 90.0%

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone (192704-56-6) → 17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester (95716-70-4)

Guidance literature:

With hexafluoropropene-diethylamine adduct; diethyl-(pentafluoro-propenyl)-amine; In chloroform; at 30 ℃; for 30h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 80.0%

methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone (192704-58-8) → 17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester (95716-70-4)

Guidance literature:

With formic acid; potassium formate; acetic anhydride; at 70 - 100 ℃; for 19h; Inert atmosphere;

upstream raw materials:

diazomethane

17β-hydroxypregna-4,9(11)-dien-3-one-7α,21-dicarboxylic acid γ-lactone

dimethyl sulfate

17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

Downstream raw materials:

eplerenone

Refernces

• 1、 -. "Preparation method of eplerenone with high efficiency and low pollution". . . Retrieved 2020/11/10.
• 2、 Dams, Iwona,Bia?ońska, Agata,Cmoch, Piotr,Krupa, Ma?gorzata,Pietraszek, Anita,Ostaszewska, Anna,Chodyński, Micha?. "Synthesis and physicochemical characterization of the process-related impurities of eplerenone, an antihypertensive drug". . . Retrieved 2017/09/01.