tert-butyl 3-oxohexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylate

Base Information

• Chemical Name: tert-butyl 3-oxohexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylate
• CAS No.: 1246551-25-6
• Molecular Formula: C₁₁H₁₉N₃O₃
• Molecular Weight: 241.29
• Mol file: 1246551-25-6.mol

Synonyms:tert-butyl 3-oxo-1,2,5,6,8,8a-hexahydroimidazo[1,5-a]pyrazine-7-carboxylate

Chemical Property of tert-butyl 3-oxohexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylate

Chemical Property:

• Melting Point: 212-213 °C
• Boiling Point: 426.6±44.0 °C(Predicted)
• PKA: 14.25±0.20(Predicted)
• Density: 1.23±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% purity ^*data from raw suppliers

7-Boc-3-oxohexahydroimidazo[1,5-a]pyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-oxohexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylate

There total 6 articles about tert-butyl 3-oxohexahydroimidazo[1,5-a]pyrazine-7(1H)-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: 90.0%

di-tert-butyl 2-(aminomethyl)piperazine-1,4-dicarboxylate (1256815-07-2,1808248-63-6,1932411-32-9) → tert-butyl 3-oxo-1,2,5,6,8,8a-hexahydroimidazo[1,5-a]pyrazine-7-carboxylate (1246551-25-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 3h; Reflux;

DOI:10.1016/j.ejmech.2010.08.002

Reference yield:

tert-butyl 1,3-dioxo-5,6,8,8a-tetrahydroimidazo[1,5-a]pyrazine-7-carboxylate → tert-butyl 3-oxo-1,2,5,6,8,8a-hexahydroimidazo[1,5-a]pyrazine-7-carboxylate (1246551-25-6)

Guidance literature:

With borane-THF; at 20 ℃;

Reference yield:

di-tert-butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)-piperazine-1,4-dicarboxylate (1256815-06-1) → tert-butyl 3-oxo-1,2,5,6,8,8a-hexahydroimidazo[1,5-a]pyrazine-7-carboxylate (1246551-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methylamine / ethanol / 4 h / Reflux

2: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Reflux

With sodium hydride; methylamine; In tetrahydrofuran; ethanol; mineral oil; 1: Mitsunobu reaction;

DOI:10.1080/00397911.2010.525774

upstream raw materials:

di-tert-butyl 2-(aminomethyl)piperazine-1,4-dicarboxylate

di-tert-butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)-piperazine-1,4-dicarboxylate

2-hydroxymethylpiperazine-1,4-dicarboxylic acid di-tert-butyl ester

tert-butyl methyl piperazine-1,3-dicarboxylate

Downstream raw materials:

tert-butyl 2-(4-chlorophenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate

tert-butyl 2-(4-cyanophenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate

tert-butyl 2-(4-(trifluoromethyl)phenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate

tert-butyl 2-(4-(methylsulfonyl)phenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate

Refernces

• 1、 Zhu, Yanyun,Song, Gonghua,Lu, Peng,Zhu, Mingjie,Chen, Yilang. "Convenient synthesis of novel 2-substituted imidazopyrazinone derivatives". experimental part. p. 469 - 479. Retrieved 2011/11/29.