rac-(13aR*)-2,3-Dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine

Base Information

• Chemical Name: rac-(13aR*)-2,3-Dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine
• CAS No.: 47206-72-4
• Molecular Formula: C19H21NO2
• Molecular Weight: 295.38
• Mol file: 47206-72-4.mol

Synonyms:rac-(13aR*)-2,3-Dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine;diMethoxyberbine

Chemical Property of rac-(13aR*)-2,3-Dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-(13aR*)-2,3-Dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine

There total 29 articles about rac-(13aR*)-2,3-Dimethoxy-5,8,13,13a-tetrahydro-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: 78.0%

2-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]isoquinolinium bromide → 2,3-dimethoxyberbine (47206-72-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In ethyl acetate; toluene; for 4h; Heating;

DOI:10.1021/ol006213a

Reference yield: 68.0%

2,3-dimethoxy-8-oxoberbine (1876-67-1) → 2,3-dimethoxyberbine (47206-72-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1016/S0040-4039(98)00744-8

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 2,3-dimethoxyberbine (47206-72-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Schotten-Baumann condensation

2: Bischler-Napieralski cyclization

3: sodium borohydride

4: 40 percent / tri-n-butylamine / palladium diacetate, triphenylphosphine / 30 h / 100 °C

5: 52 percent / lithium aluminium hydride / tetrahydrofuran / 10 h / Heating; addition at 0 deg C

With sodium tetrahydroborate; lithium aluminium tetrahydride; tributyl-amine; palladium diacetate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)92052-6

upstream raw materials:

diazomethane

3-Methoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolin-2-ol

2,3-dimethoxy-8-oxoberbine

5,6-dihydro-2,3-dimethoxy-8H-dibenzo[a,g]quinolizin-8-one

Refernces

• 1、 Singh, Kamal Nain. "2-(o-tolyl)-4,4-dimethyl-2-oxazolines - A new vehicle for facile convergent synthesis of protoberberine alkaloids". . p. 4391 - 4392. Retrieved 2007/10/03.
• 2、 Pakrashi, S. C.,Mukhopadhyay, Ranjan,Dastidar, P. P. Ghosh,Bhattacharjya, Anup,Ali, E.. "Bharatamine A Novel Protoberberine Alkaloid of Aberrant Biogenetic Origin from Alangium lamarckii Thw.". . p. 1003 - 1007. Retrieved 2007/10/02.