C₂₀H₂₅NO₅

Base Information

• Chemical Name: C₂₀H₂₅NO₅
• CAS No.: 74007-22-0
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 74007-22-0.mol

Synonyms:C₂₀H₂₅NO₅

Chemical Property of C₂₀H₂₅NO₅

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₀H₂₅NO₅

There total 5 articles about C₂₀H₂₅NO₅ 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: 100.0%

5-(2-formyl-6-methoxy-1,2,3,4,5,8-hexahydro-isoquinolin-1-ylmethyl)-2-methoxy-phenol (58780-17-9) + ethylene glycol (107-21-1) → C20H25NO5 (74007-22-0)

Guidance literature:

methanesulfonic acid; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1021/jo01303a045

Reference yield:

homoisovanillic acid (1131-94-8) → C20H25NO5 (74007-22-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / 2 h / 200 °C

2: 2)Na(CN)BH₃ / 1) cyclization, neutralization to pH 4-5 with concentrated aqueous NH₃ 2) reduction with Na(CN)BH₃ in refluxing 65percent MeOH for 1.5h

3: 90 percent / Li, NH₃ (liquid) / tetrahydrofuran; 2-methyl-propan-2-ol / 1) 4h -55 to -65 deg C 2) 1.5h -75 deg C

4: 94 percent / ethyl acetate / Heating

5: 100 percent / CH₃SO₃H / tetrahydrofuran / 1 h / 25 °C

With ammonia; lithium; sodium cyanoborohydride; methanesulfonic acid; In tetrahydrofuran; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/jo01303a045

Reference yield:

1-(3'-hydroxy-4'-methoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (23180-27-0) → C20H25NO5 (74007-22-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Li, NH₃ (liquid) / tetrahydrofuran; 2-methyl-propan-2-ol / 1) 4h -55 to -65 deg C 2) 1.5h -75 deg C

2: 94 percent / ethyl acetate / Heating

3: 100 percent / CH₃SO₃H / tetrahydrofuran / 1 h / 25 °C

With ammonia; lithium; methanesulfonic acid; In tetrahydrofuran; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/jo01303a045

upstream raw materials:

5-(2-formyl-6-methoxy-1,2,3,4,5,8-hexahydro-isoquinolin-1-ylmethyl)-2-methoxy-phenol

ethylene glycol

homoisovanillic acid

6-methoxy-1-(3-hydroxy-4-methoxybenzyl)-1,2,3,4,5,8-hexahydroisoquinoline

Downstream raw materials:

1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one

1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,6,7,8-hexahydroisoquinolin-6-one

C₂₀H₂₆BrNO₅

C₂₀H₂₅Br₂NO₅

Refernces

• 1、 Rice, Kenner C.. "Synthetic Opium Alkaloids and Derivatives. A Short Total Synthesis of (+/-)-Dihydrothebainone, (+/-)-Dihydrocodeinone, and (+/-)-Nordihydrocodeinone as an Approach to a Practical Synthesis of Morphine, Codeine, and Congeners.". . p. 3135 - 3137. Retrieved 2007/10/02.