5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione

Base Information

• Chemical Name: 5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione
• CAS No.: 867339-47-7
• Molecular Formula: C₁₅H₁₈N₂O₃
• Molecular Weight: 274.32
• Mol file: 867339-47-7.mol

Synonyms:5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione

Chemical Property of 5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione

There total 5 articles about 5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione 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: 43.0%

(2R,5R)-5-Amino-1-(4-methoxy-benzyl)-5-methyl-6-oxo-piperidine-2-carboxylic acid methyl ester; hydrochloride + Indole-3-propionic acid (830-96-6) → 5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione (867339-47-7) + rac-(2S,5S)-methyl 5-(3-1H-indol-3-yl-propionylamino)-1-(4-methoxybenzyl)-5-methyl-6-oxo-2-piperidine-carboxylate

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2005.07.085

Reference yield:

6-chloro-2-(4-methoxy-benzyl)-4-methyl-2,5-diaza-bicyclo[2.2.2]oct-5-en-3-one → 5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione (867339-47-7)

Guidance literature:

With air moisture; In toluene; for 16h;

DOI:10.1016/j.tet.2005.07.085

Reference yield:

1-(4-methoxybenzyl)-5-chloro-3-methylpyrazin-2-(1H)-one (867339-45-5) → 5-(4-methoxybenzyl)-1-methyl-2,5-diazabicyclo[2.2.2]octane-3,6-dione (867339-47-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 4 h / 145 °C / 26600 Torr

2: air moisture / toluene / 16 h

With air moisture; In toluene; 1: Diels-Alder reaction;

DOI:10.1016/j.tet.2005.07.085

upstream raw materials:

Indole-3-propionic acid

1-(4-methoxybenzyl)-5-chloro-3-methylpyrazin-2-(1H)-one

3,5-dichloro-1-(4-methoxybenzyl)pyrazin-2(1H)-one