5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane

Base Information

• Chemical Name: 5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane
• CAS No.: 873313-70-3
• Molecular Formula: C₂₃H₃₅NO₄
• Molecular Weight: 389.535
• Mol file: 873313-70-3.mol

Synonyms:5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane

Chemical Property of 5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane

There total 2 articles about 5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane 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: 70.0%

2-[2-(oxiran-2-yl)ethoxy]-2H-tetrahydropyran (88055-58-7) + 1,3-dimethyl-4-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine (123004-53-5) → 5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane (873313-70-3)

Guidance literature:

1,3-dimethyl-4-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; for 0.75h; cooling;

2-[2-(oxiran-2-yl)ethoxy]-2H-tetrahydropyran; In diethyl ether; at -5 ℃; for 0.5h;

DOI:10.1021/jm058261c

Reference yield:

2-(3-butenyloxy)tetrahydropyran (59574-65-1) → 5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane (873313-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 24 h / 0 °C

2.1: s-BuLi / tetrahydrofuran; cyclohexane / 0.75 h / cooling

2.2: 70 percent / diethyl ether / 0.5 h / -5 °C

With sec.-butyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/jm058261c

Reference yield: 70.0%

5-(3-methoxyphenyl)-8,9-dimethyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]methyl-2-oxa-8-azabicyclo[3.3.1]nonane (873313-70-3) → 3-(2-bromoethyl)-5-(3-methoxyphenyl)-8,9-dimethyl-2-oxa-8-azabicyclo[3.3.1]nonane (873313-71-4)

Guidance literature:

With bromine; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jm058261c

upstream raw materials:

2-[2-(oxiran-2-yl)ethoxy]-2H-tetrahydropyran

1,3-dimethyl-4-(3-methoxyphenyl)-1,2,5,6-tetrahydropyridine

2-(3-butenyloxy)tetrahydropyran

Downstream raw materials:

3-(2-bromoethyl)-5-(3-methoxyphenyl)-8,9-dimethyl-2-oxa-8-azabicyclo[3.3.1]nonane

acetic acid 3-bromo-1-[4-(3-methoxy-phenyl)-1,5-dimethyl-1,2,3,4-tetrahydro-pyridin-4-ylmethyl]-propyl ester