5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

Base Information

• Chemical Name: 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol
• CAS No.: 112089-72-2
• Molecular Formula: C₂₁H₂₂N₂O₃
• Molecular Weight: 350.417
• Mol file: 112089-72-2.mol

Synonyms:5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

Chemical Property of 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

There total 13 articles about 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol 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: 57.0%

acetic anhydride (108-24-7) + 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol (112243-83-1) → 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol (112089-72-2)

Guidance literature:

In diethyl ether;

DOI:10.1021/jm00398a017

Reference yield:

3-nitro-4-chlorophenol (610-78-6) → 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol (112089-72-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / K₂CO₃ / acetone; dimethylformamide / 64 h / Ambient temperature

2: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C

3: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature

4: 69 percent / hydrogen / 84.5percent PtO₂ / ethanol / 2.75 h / 2327.2 Torr

5: 111 g / pyridine / 1.42 h / 5 °C

6: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

7: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

8: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

9: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h

10: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating

11: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene

12: 57 percent / diethyl ether

With pyridine; sulfuryl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; nitric acid; sodium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; nitromethane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm00398a017

Reference yield:

2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol (106014-83-9) → 5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol (112089-72-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 69 percent / hydrogen / 84.5percent PtO₂ / ethanol / 2.75 h / 2327.2 Torr

2: 111 g / pyridine / 1.42 h / 5 °C

3: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

4: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

5: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

6: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h

7: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating

8: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene

9: 57 percent / diethyl ether

With pyridine; sulfuryl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; nitric acid; sodium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; nitromethane; ethanol; toluene;

DOI:10.1021/jm00398a017

upstream raw materials:

acetic anhydride

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

3-nitro-4-chlorophenol

2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol

Downstream raw materials:

2-acetyl-1,2,8,8a-tetrahydro-7-methylcyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methyl-3-acetylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol 1-methanesulfonate