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

Base Information

• Chemical Name: 4a-(2,3-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline
• CAS No.: 83999-50-2
• Molecular Formula: C₂₀H₂₇NO₄
• Molecular Weight: 345.439
• Mol file: 83999-50-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about 4a-(2,3-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline 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: 85.0%

4a-(2,3-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline (91713-01-8) → 4a-(2,3-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline (83999-50-2)

Guidance literature:

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

DOI:10.1021/jo00194a026

Reference yield:

1,2-dimethoxybenzene (91-16-7) → 4a-(2,3-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline (83999-50-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) n-BuLi, TMEDA / 1) hexane, ether, RT, 2 h, 2) RT, 18 h

2: 60 percent / 0.5 N H₂SO₄ / tetrahydrofuran / 20 h

3: p-toluenesulfonic acid monohydrate / benzene / 20 h / Heating

4: 1) BH₃, 2) 3N NaOH, 30 percent H₂O₂ / 1) THF, RT, overnight, 2a) 1 h, RT, 2b) 45 deg C, overnight

5: 88 percent / pyridinium chlorochromate / CH₂Cl₂

6: 1) NaH / 1) DME, 2) toluene, 36 h, reflux

7: 1) OsO₄, 2) NaIO₄ / 1) ether, water, 20 min, 2) 48 h

8: 90 percent / NaH, t-amyl alcohol / benzene / 0.5 h / Heating

9: 99 percent / sodium acetate / ethanol / Heating

10: 60 percent / p-toluenesulfonyl chloride / pyridine; H₂O / 0.75 h / Ambient temperature

11: 85 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

With sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; tert-Amyl alcohol; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; borane; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; pyridinium chlorochromate; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo00194a026

Reference yield:

3-isopropoxycyclohex-2-en-1-one (58529-72-9) → 4a-(2,3-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-2,3,4,4a,5,6,7,8-octahydroisoquinoline (83999-50-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) n-BuLi, TMEDA / 1) hexane, ether, RT, 2 h, 2) RT, 18 h

2: 60 percent / 0.5 N H₂SO₄ / tetrahydrofuran / 20 h

3: p-toluenesulfonic acid monohydrate / benzene / 20 h / Heating

4: 1) BH₃, 2) 3N NaOH, 30 percent H₂O₂ / 1) THF, RT, overnight, 2a) 1 h, RT, 2b) 45 deg C, overnight

5: 88 percent / pyridinium chlorochromate / CH₂Cl₂

6: 1) NaH / 1) DME, 2) toluene, 36 h, reflux

7: 1) OsO₄, 2) NaIO₄ / 1) ether, water, 20 min, 2) 48 h

8: 90 percent / NaH, t-amyl alcohol / benzene / 0.5 h / Heating

9: 99 percent / sodium acetate / ethanol / Heating

10: 60 percent / p-toluenesulfonyl chloride / pyridine; H₂O / 0.75 h / Ambient temperature

11: 85 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

With sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; tert-Amyl alcohol; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; borane; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; pyridinium chlorochromate; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo00194a026

upstream raw materials:

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

1,2-dimethoxybenzene

3-isopropoxycyclohex-2-en-1-one

1,3-cylohexanedione

Downstream raw materials:

(3aS,7aS,7bS)-3a-(2,3-Dimethoxy-phenyl)-1a-methyl-5-oxo-decahydro-1a-azonia-cyclopropa[a]naphthalene; perchlorate

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

Refernces