Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-8a-methyl-, (8aS)- (9CI)

Base Information

• Chemical Name: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-8a-methyl-, (8aS)- (9CI)
• CAS No.: 847952-36-7
• Molecular Formula: C₈H₁₂N₂O₂
• Molecular Weight: 168.195
• Mol file: 847952-36-7.mol

Synonyms:Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-8a-methyl-, (8aS)- (9CI);(8aS)-hexahydro-8a-Methyl-Pyrrolo[1,2-a]pyrazine-1,4-dione

Chemical Property of Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-8a-methyl-, (8aS)- (9CI)

Chemical Property:

• PSA: 49.41000
• LogP: -0.23600

Purity/Quality:

99% ^*data from raw suppliers

(8AS)-Hexahydro-8a-methylpyrrolo-[1,2-a]pyrazine-1,4-dione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-8a-methyl-, (8aS)- (9CI)

There total 6 articles about Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-8a-methyl-, (8aS)- (9CI) 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: 98.0%

(S)-methyl 1-(2-(((benzyloxy)carbonyl)amino)acetyl)-2-methylpyrrolidine-2-carboxylate (847952-40-3) → (8aS)-8a-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (847952-36-7,1638744-87-2)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 20 ℃; for 15h;

Reference yield:

methyl (S)-2-methylpyrrolidine-2-carboxylate monohydrochloride (220060-08-2,51098-46-5,1286768-32-8) → (8aS)-8a-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (847952-36-7,1638744-87-2)

Guidance literature:

Multi-step reaction with 2 steps

1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 20.5 h / 20 °C / Inert atmosphere

2: hydrogen; palladium 10% on activated carbon / methanol / 15 h / 20 °C

With palladium 10% on activated carbon; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In methanol; dichloromethane;

Reference yield:

C9H16N2O3 → (8aS)-8a-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (847952-36-7,1638744-87-2)

Guidance literature:

With triethylamine; In methanol; for 6h; Reflux;

DOI:10.1016/j.bmcl.2010.10.061

upstream raw materials:

(S)-methyl 1-(2-(((benzyloxy)carbonyl)amino)acetyl)-2-methylpyrrolidine-2-carboxylate

(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

(3R,7aS)-7a-methyl-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one

methyl (S)-2-methylpyrrolidine-2-carboxylate monohydrochloride

Refernces

• 1、 -. "NEUROPROTECTIVE BICYCLIC COMPOUNDS AND METHODS FOR THEIR USE IN TREATING AUTISM SPECTRUM DISORDERS AND NEURODEVELOPMENTAL DISORDERS". Page/Page column 38-39. . Retrieved 2015/02/19.
• 2、 Moir, Elizabeth M.,Yoshiizumi, Kazuya,Cairns, Jim,Cowley, Phillip,Ferguson, Morag,Jeremiah, Fiona,Kiyoi, Takao,Morphy, Richard,Tierney, Jason,Wishart, Grant,York, Mark,Baker, James,Cottney, Jean E.,Houghton, Andrea K.,McPhail, Petula,Osprey, Andrew,Walker, Glenn,Adam, Julia M.. "Design, synthesis, and structure-activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists". scheme or table. p. 7327 - 7330. Retrieved 2011/01/12.