3-Oxo-4-aza-11a-Methoxy-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester

Base Information

• Chemical Name: 3-Oxo-4-aza-11a-Methoxy-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester
• CAS No.: 1026013-15-9
• Molecular Formula: C₂₁H₃₁NO₄
• Molecular Weight: 361.481
• Mol file: 1026013-15-9.mol

Synonyms:

Chemical Property of 3-Oxo-4-aza-11a-Methoxy-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

3-Oxo-4-aza-11a-methoxy-5α-αndrost-1-ene-17β-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3-Oxo-4-aza-11a-methoxy-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester is an intermediate in the synthesis of Finasteride (F342000), an inhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone.

Technology Process of 3-Oxo-4-aza-11a-Methoxy-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester

There total 1 articles about 3-Oxo-4-aza-11a-Methoxy-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester 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:

methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate (103335-41-7) → (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 (1026013-15-9)

Guidance literature:

With lithium trifluoromethanesulfonate; In methanol; electrochemical reaction; cathode: stainless steel, anode: carbon felt; constant current of 200 mA;

DOI:10.1021/jo00121a067

Reference yield:

(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 (1026013-15-9) → Methyl 3-oxo-4-azaandrosta-1,5,7-triene-17β-carboxylate (166896-63-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 16 h / 100 °C

2: DDQ / CH₂Cl₂; acetonitrile / -40 °C

3: CH₂Cl₂; acetonitrile / 18 h / 20 °C

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; acetonitrile;

DOI:10.1021/jo00121a067

Reference yield:

(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 (1026013-15-9) → Methyl 3-oxo-4-azaandrosta-1,5-diene-17β-carboxylate (166896-62-4)

Guidance literature:

at 100 ℃; for 16h; Yield given;

DOI:10.1021/jo00121a067

upstream raw materials:

methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate

Downstream raw materials:

Methyl 3-oxo-4-azaandrosta-1,5-diene-17β-carboxylate

Methyl 3-oxo-4-azaandrosta-1,5,7-triene-17β-carboxylate

Refernces