1-methyl-5-<3-(endo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone

Base Information

• Chemical Name: 1-methyl-5-<3-(endo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone
• CAS No.: 115919-88-5
• Molecular Formula: C₂₂H₂₄N₂O₃
• Molecular Weight: 364.444
• Mol file: 115919-88-5.mol

Synonyms:

Chemical Property of 1-methyl-5-<3-(endo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-methyl-5-<3-(endo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone

There total 9 articles about 1-methyl-5-<3-(endo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone 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:

3,4-Dihydro-1H-1,4-methano-naphthalen-2-one (7374-90-5) → 1-methyl-5-<3-(endo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone (115919-88-5,131486-58-3,131486-59-4,131486-70-9,131486-71-0)

Guidance literature:

Multi-step reaction with 8 steps

1: p-toluenesulfonic acid, 3A sieves / toluene / 15 h / Heating

2: LiAlH₄, AlCl₃ / diethyl ether / 0.5 h / 0 °C

3: Br₂ / CHCl₃

4: K₂CO₃ / dimethylformamide / 15 h

5: 1.) tert-butyl lithium / 1.) THF, pentane, -78 deg C, 1.5 h, 2.) a) -78 deg C, 0.5 h, b) from -78 deg C to RT

6: ethanol; H₂O / 72 h

7: Dibal-H / toluene / 4 h / -78 °C

8: tetrahydrofuran / 40 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; 3 A molecular sieve; bromine; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00105a045

Reference yield:

3-exo-benzobicyclo<2.2.1>hept-2-yl formate (69618-83-3,69651-91-8,113034-45-0,131486-60-7) → 1-methyl-5-<3-(exo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone (115919-88-5,131486-58-3,131486-59-4,131486-70-9,131486-71-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 29.3 percent / p-toluenesulfonic acid / chlorobenzene / 40 h / Heating

2: ethanol; H₂O / 72 h

3: dibal- H / toluene / 4 h / -78 °C

4: tetrahydrofuran / 40 h / Ambient temperature

With diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; water; chlorobenzene; toluene;

DOI:10.1021/jm00105a045

Reference yield:

4-Bromo-2-[(1S,2S,4S)-(1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl)oxy]-phenol (115898-54-9,131486-66-3) → 1-methyl-5-<3-(endo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxyphenyl>-2-imidazolidinone (115919-88-5,131486-58-3,131486-59-4,131486-70-9,131486-71-0)

Guidance literature:

Multi-step reaction with 5 steps

1: K₂CO₃ / dimethylformamide / 15 h

2: 1.) tert-butyl lithium / 1.) THF, pentane, -78 deg C, 1.5 h, 2.) a) -78 deg C, 0.5 h, b) from -78 deg C to RT

3: ethanol; H₂O / 72 h

4: Dibal-H / toluene / 4 h / -78 °C

5: tetrahydrofuran / 40 h / Ambient temperature

With tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00105a045

upstream raw materials:

3-exo-benzobicyclo<2.2.1>hept-2-yl formate

1-methyl-3-(exo-benzobicyclo<2.2.1>hept-2-yloxy)-4-methoxybenzaldehyde

{4-Methoxy-3-[(1S,2R,4S)-(1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl)oxy]-phenyl}-methylamino-acetonitrile

1-{4-Methoxy-3-[(1S,2S,4S)-(1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl)oxy]-phenyl}-N¹-methyl-ethane-1,2-diamine

Refernces