(5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile

Base Information

Chemical Name:(5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile
CAS No.:385440-33-5
Molecular Formula:C₂₀H₁₉F₃N₄O₄
Molecular Weight:436.39
Hs Code.:

Synonyms:(5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile

There total 6 articles about (5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile 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:

: 74844-91-0
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

: 385440-33-5
(5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / pyridine / CH₂Cl₂

2: 100 percent / LiBH₄ / tetrahydrofuran / 22 °C

3: (COCl)2; DMSO; TEA / CH₂Cl₂ / -78 - 0 °C

4: CH₂Cl₂

5: 99 percent / DBU / 1,2-dichloro-ethane / 80 °C

6: aq. NaOH

7: HCl

8: H₂ / Pd/C / ethyl acetate

9: 1,2-dichloro-ethane / 22 °C

10: DBU / 1,2-dichloro-ethane / 2 h / 60 °C

With pyridine; hydrogenchloride; sodium hydroxide; lithium borohydride; oxalyl dichloride; TEA; hydrogen; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; 3: Swern oxidation;
DOI:10.1016/j.bmcl.2004.09.049

Reference yield:

: 385440-70-0
(2S,4R)-2-Formyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 385440-33-5
(5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile

Guidance literature:: Multi-step reaction with 7 steps

1: CH₂Cl₂

2: 99 percent / DBU / 1,2-dichloro-ethane / 80 °C

3: aq. NaOH

4: HCl

5: H₂ / Pd/C / ethyl acetate

6: 1,2-dichloro-ethane / 22 °C

7: DBU / 1,2-dichloro-ethane / 2 h / 60 °C

With hydrogenchloride; sodium hydroxide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2004.09.049

Reference yield:

: (1S,4S)-5-Benzyl-2,5-diaza-bicyclo[2.2.1]heptane-2,6-dicarboxylic acid 2-tert-butyl ester

: 385440-33-5
(5S,8S,8aR)-4-[Octahydro-7-[(1,1-dimethylethoxy)-carbonyl]-1,3-dioxo-5,8-methanoimidazo[1,5-a]pyrazin-2-yl]-2-(trifluoromethyl)-benzonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: HCl

2: H₂ / Pd/C / ethyl acetate

3: 1,2-dichloro-ethane / 22 °C

4: DBU / 1,2-dichloro-ethane / 2 h / 60 °C

With hydrogenchloride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In ethyl acetate; 1,2-dichloro-ethane;
DOI:10.1016/j.bmcl.2004.09.049