7,8-Dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo(1,2-b)isoquinoline

Base Information

• Chemical Name: 7,8-Dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo(1,2-b)isoquinoline
• CAS No.: 82589-55-7
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• NSC Number: 321159
• Mol file: 82589-55-7.mol

Synonyms:82589-55-7;7,8-Dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo(1,2-b)isoquinoline;NSC 321159;BRN 4691333;7,8-dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline;NSC321159;Pyrrolo(1,2-b)isoquinoline, 1,2,3,5,10,10a-hexahydro-7,8-dimethoxy-;NSC-321159;7,8-dimethoxy-2,3,4,5,10,10a-hexahydro-1H-pyrrolo[1,2-b]isoquinoline

Chemical Property of 7,8-Dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo(1,2-b)isoquinoline

Chemical Property:

• Vapor Pressure: 5.76E-05mmHg at 25°C
• Boiling Point: 346.4°C at 760 mmHg
• Flash Point: 127.7°C
• Density: 1.15g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 271

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2CN3CCCC3CC2=C1)OC

Technology Process of 7,8-Dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo(1,2-b)isoquinoline

There total 15 articles about 7,8-Dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo(1,2-b)isoquinoline 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: 55.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-Amino-1-phenylethanol (7568-93-6,1936-63-6) → 7,8-Dimethoxy-1,2,3,5,10,10a-hexahydropyrrolo<1,2-b>isoquinoline (82589-55-7)

Guidance literature:

With hydrogenchloride; In ethanol; for 6h; Heating;

DOI:10.1021/jo00196a001

Reference yield:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → 2,3-Dimethoxy-5,7,8,9,9a,10-hexahydro-pyrrolo<1,2-b>isochinolin (82589-55-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / 1.) triethylamine, 2.) DCCD / CH₂Cl₂ / 60 h / 20 °C

2: 1.) triethyloxonium-tetrafuoroborate, 2.) NaBH₄ / 1.) CH₂Cl₂, room temp., 24 h; 2.) ethanol, room temp., 15 h

3: 66 percent / conc. aq. HCl / 1 h / Heating

4: 61 percent / PPA, POCl₃ / 4 h / 100 °C

5: 92 percent / NaBH₄ / dioxane; tetrahydrofuran; methanol

6: 1.) pyridine 2.) H₂ / 2.) 10percent Pd/C / 1.) room temp., 3.5 h; 2.) glacial acetic acid, room temp., 10 at, 15 min; 60 deg C, 10 at, 5 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; hydrogen; triethyloxonium fluoroborate; triethylamine; dicyclohexyl-carbodiimide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1002/ardp.19833160909

Reference yield:

Veratric acid (93-07-2) → 2,3-Dimethoxy-5,7,8,9,9a,10-hexahydro-pyrrolo<1,2-b>isochinolin (82589-55-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / 1.) triethylamine, 2.) DCCD / CH₂Cl₂ / 60 h / 20 °C

2: 1.) triethyloxonium-tetrafuoroborate, 2.) NaBH₄ / 1.) CH₂Cl₂, room temp., 24 h; 2.) ethanol, room temp., 15 h

3: 66 percent / conc. aq. HCl / 1 h / Heating

4: 61 percent / PPA, POCl₃ / 4 h / 100 °C

5: 92 percent / NaBH₄ / dioxane; tetrahydrofuran; methanol

6: 1.) pyridine 2.) H₂ / 2.) 10percent Pd/C / 1.) room temp., 3.5 h; 2.) glacial acetic acid, room temp., 10 at, 15 min; 60 deg C, 10 at, 5 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; hydrogen; triethyloxonium fluoroborate; triethylamine; dicyclohexyl-carbodiimide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1002/ardp.19833160909

upstream raw materials:

formaldehyd

2-Amino-1-phenylethanol

2-(3,4-dimethoxy-benzyl)-pyrrolidine

4-Amino-5-(3,4-dimethoxy-phenyl)-pentan-1-ol