(13R,13aR)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine

Base Information

• Chemical Name: (13R,13aR)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine
• CAS No.: 6901-07-1
• Molecular Formula: C22H27NO4
• Molecular Weight: 0
• Mol file: 6901-07-1.mol

Synonyms:Mesocorydalin;(13R-cis)-5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine;2,3,9,10-Tetramethoxy-13β-methyl-13aβ-berbin;(13R,13aR)-2,3,9,10-Tetramethoxy-13-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline;6H-Dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-13-methyl-, (13R-cis)-;d-Mesocorydalin;

Chemical Property of (13R,13aR)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine

Chemical Property:

• PSA: 40.16000
• LogP: 3.87540

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (13R,13aR)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine

There total 15 articles about (13R,13aR)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine 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: 54.0%

2-<2,3-dimethoxy-6-(1'-trimethylsilylethyl)benzyl>-6,7-dimethoxy-3,4-dihydroisoquinolinium perchlorate → mesocorydaline (518-69-4,6018-35-5,6018-36-6,6018-38-8,6901-07-1,71213-90-6) + trans-(+-)-5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine (6018-35-5)

Guidance literature:

In methanol; for 24h; Irradiation;

Reference yield:

→ mesocorydaline (518-69-4,6018-35-5,6018-36-6,6018-38-8,6901-07-1,71213-90-6) + trans-(+-)-5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine (6018-35-5)

Guidance literature:

With ethanol; sulfuric acid; zinc; at 20 ℃;

Reference yield:

N,N-dimethyl-N-(1-(3',4'-dimethoxyphenyl)ethyl)amine (139577-08-5) → mesocorydaline (518-69-4,6018-35-5,6018-36-6,6018-38-8,6901-07-1,71213-90-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) BuLi / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 24 h

2: 81 percent / diisopropylethylamine / dimethylformamide / 2 h / 25 °C

3: 96 percent / ethyl chloroformate / tetrahydrofuran / 3 h / 0 °C

4: 1.) Mg, 2.) 0.5percent H₂SO₄ / 1.) THF, 25 deg C, 12 h, 2.) MeOH, ether, 25 deg C, 2 h

5: 93 percent / NaI, trimethylsilyl chloride / acetonitrile / 0.5 h / 25 °C

6: 68 percent / AgClO₄ / acetonitrile / 24 h / 25 °C

7: 33 percent / methanol / 24 h / Irradiation

With n-butyllithium; chloro-trimethyl-silane; sulfuric acid; silver perchlorate; chloroformic acid ethyl ester; magnesium; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

(1R)-3endo-bromo-2-oxo-bornane-8-sulfonic acid

mesocorydaline

dehydrocorydaline

3,5-dihydroxyphenol

Downstream raw materials:

2,3,9,10-tetramethoxy-13α-methyl-13aα-berbine

Refernces