Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate

Base Information

• Chemical Name: Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate
• CAS No.: 1053265-72-7
• Molecular Formula: C₂₉H₃₅ClN₂O₂
• Molecular Weight: 479.062
• Mol file: 1053265-72-7.mol

Synonyms:Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate

Chemical Property of Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate

There total 6 articles about Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate 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:

methyl (4aR)-3-[(2-bromo-5,5-dimethyl-1-cyclohexen-1-yl)methyl]-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate (1053265-71-6) + 4-Chlorophenylboronic acid (1679-18-1) → Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate (1053265-72-7)

Guidance literature:

With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 80 ℃; for 16.25h;

Reference yield:

4,4-dimethylcyclohexenone (1073-13-8) → Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate (1053265-72-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr

2.1: phosphorus tribromide / dichloromethane / 0.5 h / 0 - 20 °C

2.2: 4 h / 0 - 20 °C

3.1: sodium tetrahydroborate / methanol / 5 h / 0 - 20 °C

4.1: phosphorus tribromide / diethyl ether / 1.5 h / 0 °C

5.1: triethylamine; sodium iodide / N,N-dimethyl-formamide / 3 h / 80 °C

6.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; ethanol; water / 16.25 h / 80 °C

With sodium tetrahydroborate; hydrogen; phosphorus tribromide; sodium carbonate; triethylamine; sodium iodide; bis-triphenylphosphine-palladium(II) chloride; 5%-palladium/activated carbon; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

(2-bromo-5,5-dimethyl-1-cyclohexen-1-yl)-methanol (1053265-67-0) → Methyl (4aR)-3-{[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate (1053265-72-7)

Guidance literature:

Multi-step reaction with 3 steps

1: phosphorus tribromide / diethyl ether / 1.5 h / 0 °C

2: triethylamine; sodium iodide / N,N-dimethyl-formamide / 3 h / 80 °C

3: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; ethanol; water / 16.25 h / 80 °C

With phosphorus tribromide; sodium carbonate; triethylamine; sodium iodide; bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; diethyl ether; ethanol; water; N,N-dimethyl-formamide;

upstream raw materials:

methyl (4aR)-3-[(2-bromo-5,5-dimethyl-1-cyclohexen-1-yl)methyl]-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylate

4-Chlorophenylboronic acid

4,4-dimethylcyclohexenone

2-bromo-5,5'-bis-methylcyclohex-1-enylcarbaldehyde

Downstream raw materials:

(4aR)-3-([2-(4-Chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl}-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline-8-carboxylic acid hydrochloride