{2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester

Base Information

• Chemical Name: {2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester
• CAS No.: 735270-15-2
• Molecular Formula: C₂₅H₃₀BrNO₅
• Molecular Weight: 504.421
• Mol file: 735270-15-2.mol

Synonyms:{2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester

Chemical Property of {2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester

There total 12 articles about {2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester 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: 100.0%

{2-[1-(3,4-dimethoxy-phenyl)-4-trimethylsilanyloxy-cyclohex-3-enyl]-ethyl}-methyl-carbamic acid benzyl ester (735270-13-0) → {2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester (735270-15-2)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2004.05.021

Reference yield:

dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate (61330-09-4) → {2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester (735270-15-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 89 percent / NaH / 1,2-dimethoxy-ethane / 3 h / Heating

2.1: 87 percent / NaCl; H₂O / dimethylsulfoxide / 6 h / 140 °C

3.1: 95 percent / PPTS / benzene / 3 h / Heating

4.1: 100 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 82 percent / NaNH₂ / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

6.1: BH₃*Me₂S / tetrahydrofuran / 0 °C

6.2: 75 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O

7.1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8.1: tetrahydrofuran; H₂O / 2 h / 80 °C

9.1: 88 percent / K₂CO₃ / 4 h / 0 - 20 °C

10.1: 85 percent / H₂SO₄ / acetone; H₂O / 24 h / Heating

11.1: 100 percent / Et₃N / acetonitrile / 2 h / Heating

12.1: 100 percent / NBS / tetrahydrofuran / 0.17 h / 0 °C

With N-Bromosuccinimide; dimethylsulfide borane complex; sulfuric acid; water; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; sodium amide; triethylamine; sodium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile; benzene; 1.1: Dieckmann condensation / 2.1: Krapcho's demethoxycarbonylation / 5.1: Wittig reaction;

DOI:10.1016/j.tetlet.2004.05.021

Reference yield:

4-(3,4-dimethoxyphenyl)-4-cyanocyclohexanone (51533-65-4) → {2-[3-bromo-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohexyl]-ethyl}-methyl-carbamic acid benzyl ester (735270-15-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / PPTS / benzene / 3 h / Heating

2.1: 100 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 82 percent / NaNH₂ / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

4.1: BH₃*Me₂S / tetrahydrofuran / 0 °C

4.2: 75 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O

5.1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6.1: tetrahydrofuran; H₂O / 2 h / 80 °C

7.1: 88 percent / K₂CO₃ / 4 h / 0 - 20 °C

8.1: 85 percent / H₂SO₄ / acetone; H₂O / 24 h / Heating

9.1: 100 percent / Et₃N / acetonitrile / 2 h / Heating

10.1: 100 percent / NBS / tetrahydrofuran / 0.17 h / 0 °C

With N-Bromosuccinimide; dimethylsulfide borane complex; sulfuric acid; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; sodium amide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; acetonitrile; benzene; 3.1: Wittig reaction;

DOI:10.1016/j.tetlet.2004.05.021

upstream raw materials:

{2-[1-(3,4-dimethoxy-phenyl)-4-trimethylsilanyloxy-cyclohex-3-enyl]-ethyl}-methyl-carbamic acid benzyl ester

dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate

4-(3,4-dimethoxyphenyl)-4-cyanocyclohexanone

5-cyano-5-(3,4-dimethoxy-phenyl)-2-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Downstream raw materials:

{2-[1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid benzyl ester