methyl 3-benzyl-6-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylate

Base Information

• Chemical Name: methyl 3-benzyl-6-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylate
• CAS No.: 127073-68-1
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 127073-68-1.mol

Synonyms:methyl 3-benzyl-6-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylate

Chemical Property of methyl 3-benzyl-6-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-benzyl-6-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylate

There total 5 articles about methyl 3-benzyl-6-oxo-3-azabicyclo[3.3.1]nonane-1-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: 82.0%

2-trimethylsilyloxy-1,3-butadiene (38053-91-7) + methyl 2-((benzyl(cyanomethyl)amino)methyl)acrylate (127073-67-0) → (1S,5S)-3-Benzyl-6-oxo-3-aza-bicyclo[3.3.1]nonane-1-carboxylic acid methyl ester (127073-68-1)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -70 - 20 ℃;

DOI:10.1016/S0040-4039(01)80557-8

Reference yield: 46.0%

2-trimethylsilyloxy-1,3-butadiene (38053-91-7) + methyl 2-((benzyl(cyanomethyl)amino)methyl)acrylate (127073-67-0) → methyl 3-benzyl-6-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylate (127073-68-1)

Guidance literature:

methyl 2-((benzyl(cyanomethyl)amino)methyl)acrylate; With titanium tetrachloride; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

2-trimethylsilyloxy-1,3-butadiene; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

With water; ammonium chloride; In dichloromethane;

DOI:10.1016/j.tet.2012.05.037

Reference yield:

methyl 2-(bromomethyl)propenoate (4224-69-5) → (1S,5S)-3-Benzyl-6-oxo-3-aza-bicyclo[3.3.1]nonane-1-carboxylic acid methyl ester (127073-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) 1 eq. NEt₃ / 1.) CHCl₃, rt; 2.) CHCl₃, reflux

2: 82 percent / 4 eq. TiCl₄ / CH₂Cl₂ / -70 - 20 °C

With titanium tetrachloride; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(01)80557-8

upstream raw materials:

2-trimethylsilyloxy-1,3-butadiene

methyl 2-((benzyl(cyanomethyl)amino)methyl)acrylate

methyl 2-(bromomethyl)propenoate

benzylamine