Isoquinolinium,4a-(3,4-dimethoxyphenyl)-3,4,4a,5,6,7,8,8a-octahydro-2-methyl-6-oxo-,cis-, perchlorate

Base Information

• Chemical Name: Isoquinolinium,4a-(3,4-dimethoxyphenyl)-3,4,4a,5,6,7,8,8a-octahydro-2-methyl-6-oxo-,cis-, perchlorate
• CAS No.: 88176-91-4
• Molecular Formula: C18H24NO3.ClO4
• Molecular Weight: 401.844
• Mol file: 88176-91-4.mol

Synonyms:

Chemical Property of Isoquinolinium,4a-(3,4-dimethoxyphenyl)-3,4,4a,5,6,7,8,8a-octahydro-2-methyl-6-oxo-,cis-, perchlorate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Isoquinolinium,4a-(3,4-dimethoxyphenyl)-3,4,4a,5,6,7,8,8a-octahydro-2-methyl-6-oxo-,cis-, perchlorate

There total 14 articles about Isoquinolinium,4a-(3,4-dimethoxyphenyl)-3,4,4a,5,6,7,8,8a-octahydro-2-methyl-6-oxo-,cis-, perchlorate 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: 80.0%

4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline (88176-89-0) → cis-4a-(3,4-dimethoxyphenyl)-2-methyl-6-oxo-3,4,4a,5,6,7,8,8a-octahydroisoquinolinium perchlorate (88176-91-4)

Guidance literature:

With perchloric acid; In diethyl ether; ethanol; for 48h; Ambient temperature;

DOI:10.1021/jo00194a026

Reference yield:

3-Ethoxycyclohex-2-en-1-one (5323-87-5) → cis-4a-(3,4-dimethoxyphenyl)-2-methyl-6-oxo-3,4,4a,5,6,7,8,8a-octahydroisoquinolinium perchlorate (88176-91-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) n-BuLi, 2) glacial acetic acid, 10percent aq. HCl / 1a) ether/hexane, -60 deg C, 1 h, 1b) RT, overnight

2: pyridinium p-toluenesulfonate / benzene / 120 h / Heating

3: 1) B₂H₆, 2) 3N NaOH, 30 percent H₂O₂ / 1) THF, RT, overnight, 2a) 45 deg C, 5 h, 2b) RT

4: sodium acetate, pyridinium chlorochromate / CH₂Cl₂

5: 1) NaH / 1) DME, 3 h, RT, 2a) RT, overnight, 2b) 3 h, reflux

6: NaIO₄/KMnO₄/K₂CO₃ / dioxane; H₂O / 48 h / Ambient temperature

7: 1N KOH / ethanol / 2 h / Heating

8: 100 percent / sodium acetate / ethanol / 40 h / Heating

9: 40 percent / p-toluenesulfonyl chloride / pyridine; H₂O / 1 h / Ambient temperature

10: LiAlH₄ / tetrahydrofuran / 2 h / Heating

11: 80 percent / 70percent aq. HClO₄ / diethyl ether; ethanol / 48 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; potassium permanganate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; acetic acid; p-toluenesulfonyl chloride; pyridinium chlorochromate; diborane; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo00194a026

Reference yield:

3-(3,4-dimethoxyphenyl)-1,4-cyclohexanedione-1-(ethylene acetal) (88176-84-5) → cis-4a-(3,4-dimethoxyphenyl)-2-methyl-6-oxo-3,4,4a,5,6,7,8,8a-octahydroisoquinolinium perchlorate (88176-91-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) NaH / 1) DME, 3 h, RT, 2a) RT, overnight, 2b) 3 h, reflux

2: NaIO₄/KMnO₄/K₂CO₃ / dioxane; H₂O / 48 h / Ambient temperature

3: 1N KOH / ethanol / 2 h / Heating

4: 100 percent / sodium acetate / ethanol / 40 h / Heating

5: 40 percent / p-toluenesulfonyl chloride / pyridine; H₂O / 1 h / Ambient temperature

6: LiAlH₄ / tetrahydrofuran / 2 h / Heating

7: 80 percent / 70percent aq. HClO₄ / diethyl ether; ethanol / 48 h / Ambient temperature

With potassium hydroxide; potassium permanganate; sodium periodate; lithium aluminium tetrahydride; perchloric acid; sodium acetate; sodium hydride; potassium carbonate; p-toluenesulfonyl chloride; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; ethanol; water;

DOI:10.1021/jo00194a026

upstream raw materials:

4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline

3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one

3-Ethoxycyclohex-2-en-1-one

4-Bromoveratrole

Refernces

• 1、 McMurry, John E.,Farina, Vittorio. "TOTAL SYNTHESIS OF O-METHYLPALLIDININE". . p. 4653 - 4656. Retrieved 2007/10/02.