(4aR,4bS,6aS,7S,9aS,9bS,11aR)-methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate

Base Information

• Chemical Name: (4aR,4bS,6aS,7S,9aS,9bS,11aR)-methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate
• CAS No.: 103335-41-7
• Molecular Formula: C20H29NO3
• Molecular Weight: 331.455
• European Community (EC) Number: 600-422-0
• UNII: DDK98J5FUO
• DSSTox Substance ID: DTXSID40451476
• Nikkaji Number: J681.261I
• Wikidata: Q76416420
• ChEMBL ID: CHEMBL574911
• Mol file: 103335-41-7.mol

Synonyms:103335-41-7;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate;Dutasteride methyl ester;DDK98J5FUO;CHEMBL574911;methyl (1S,3aS,3bS,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxylate;3-Oxo-4-aza-5alpha-alphandrost-1-ene-17beta-carboxylic Acid Methyl Ester;1H-Indeno(5,4-f)quinoline-7-carboxylic acid, 2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, methyl ester, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-;CID 11002070;Methyl 4-aza-5alpha-Androsta-1-en-3-one-17beta-Carboxylate;UNII-DDK98J5FUO;CHEMBL77910;SCHEMBL797723;Dutasteride methyl ester [USP];DTXSID40451476;WMSQGMYJYBSBKA-ALHYADCGSA-N;BDBM50025344;AKOS015966768;FINASTERIDE IMPURITY B [EP IMPURITY];17beta-(Methoxycarbonyl)-4-aza-5alpha-androst-1-en-3-one;Methyl (5alpha,17beta)-3-oxo-4-azaandrost-1-ene-17-carboxylate;17.BETA.-(METHOXYCARBONYL)-4-AZA-5.ALPHA.-ANDROST-1-EN-3-ONE;3-Oxo-4-aza-5alpha-androst-1-ene-17beta-carboxylic acid methyl ester;3-Oxo-4-aza-5 alpha - alpha ndrost-1-ene-17 beta -carboxylic Acid Methyl Ester;4-Azaandrost-1-ene-17-carboxylic acid, 3-oxo-, methyl ester, (5alpha,17beta)-;METHYL (5.ALPHA.,17.BETA.)-3-OXO-4-AZAANDROST-1-ENE-17-CARBOXYLATE;Methyl 3-Oxo-4-aza-5alpha-androst-1-ene-17beta-carboxylate (Delta-1-Aza Ester);(4aR,4bS,6aS,7S,9aS,9bS,11aR)-methyl4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate;4-AZAANDROST-1-ENE-17-CARBOXYLIC ACID, 3-OXO-, METHYL ESTER, (5.ALPHA.,17.BETA.)-;4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid methyl ester

Chemical Property of (4aR,4bS,6aS,7S,9aS,9bS,11aR)-methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 280-282 °C (dec.)
• Refractive Index: 1.525
• Boiling Point: 478.615 °C at 760 mmHg
• PKA: 14.15±0.70(Predicted)
• Flash Point: 243.258 °C
• PSA: 55.40000
• Density: 1.114 g/cm³
• LogP: 3.40160
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 331.21474379
• Heavy Atom Count: 24
• Complexity: 600

Purity/Quality:

99% ^*data from raw suppliers

3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)OC)CCC4C3(C=CC(=O)N4)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)OC)CC[C@@H]4[C@@]3(C=CC(=O)N4)C
• Uses: Finasteride (F342000) and Dutasteride (D735000) impurity. An intermediate in the synthesis of Finasteride and Dutasteride, 5α-reductase inhibitors used for treatment of benign prostatic hyperplasia ac ne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders. 3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester (Finasteride EP Impurity B) is an impurity of Finasteride (F342000) and Dutasteride (D735000). An intermediate in the synthesis of Finasteride and Dutasteride, 5α-reductase inhibitors used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders. Finasteride impurity. Finasteride (F342000) impurity. A novel intermediate in the synthesis of Finasteride, a 5α-reductase inhibitor used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders.

Technology Process of (4aR,4bS,6aS,7S,9aS,9bS,11aR)-methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate

There total 9 articles about (4aR,4bS,6aS,7S,9aS,9bS,11aR)-methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-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: 91.0%

methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate (149198-45-8) → methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate (103335-41-7)

Guidance literature:

With Oxone; sodium hydrogencarbonate; In methanol; water; at 30 ℃; for 3h; Time;

Reference yield: 89.35%

methanol (67-56-1) + 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid (104239-97-6) → methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate (103335-41-7)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 14h;

Reference yield:

C20H30BrNO3 → methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate (103335-41-7)

Guidance literature:

With potassium tert-butylate; acetic acid; In DMF (N,N-dimethyl-formamide); at -5 - 8 ℃; for 0.25h;

upstream raw materials:

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

benzeneseleninic anhydride

methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate

methanol

Downstream raw materials:

3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid

(5α,17β)-N-Methoxy-N-methyl-3-oxo-4-aza-androst-1-ene-17β-carboxamide

(4aR,4bS,6aS,7S,9aS,9bS)-11a-Methoxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid methyl ester

3-Oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxylic acid

Refernces

• 1、 -. "Method for forming double bonds between 1-position and 2-position during synthesis of finasteride and dutasteride". Paragraph 0064; 0065; 0066. . Retrieved 2016/12/01.
• 2、 -. "METHOD OF PRODUCING 17BETA-(SUBSTITUTED)-3-OXO-DELTA 1,2-4-AZASTEROIDS AND INTERMEDIATES". Page 11. . Retrieved 2008/06/13.