tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate

Base Information

Chemical Name:tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate
CAS No.:1409944-11-1
Molecular Formula:C₂₀H₂₁F₂N₃O₃
Molecular Weight:389.402
Hs Code.:

Synonyms:tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate

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Chemical Property of tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate

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Technology Process of tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate

There total 13 articles about tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate 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: 66.0%

: 1409944-10-0
(E)-methyl 2-((8S,9S)-9-(tert-butoxycarbonylamino)-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylidene)acetate

: 1409944-11-1
tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate

Guidance literature:: With ozone; dimethylsulfide; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

Reference yield:

: 1409944-03-1
(S)-1,2-difluoro-3-(1-nitrohex-5-en-2-yl)benzene

: 1409944-11-1
tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium methylate / methanol / 0.5 h / 0 °C / Inert atmosphere

1.2: 4 h / -60 - -20 °C

1.3: 18 h / 20 °C

2.1: titanium(IV) tetraethanolate / benzene; tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

3.2: 2 h / -75 °C

4.1: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 20 °C

5.1: triethylamine / dichloromethane / 2 h / 20 °C

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / Inert atmosphere; Reflux

7.1: N-Methyldicyclohexylamine / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 2.02 h / 20 - 160 °C / Microwave irradiation; Inert atmosphere

8.1: ozone / dimethylsulfide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; N-Methyldicyclohexylamine; sodium methylate; ozone; triethylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; dimethylsulfide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; benzene; 6.1: Grubbs' metathesis conditions / 7.1: Heck Reaction;

Reference yield:

: 1409944-05-3
(R,E)-N-((S)-2-(2,3-difluorophenyl)hex-5-enylidene)-2-methylpropane-2-sulfinamide

: 1409944-11-1
tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

1.2: 2 h / -75 °C

2.1: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 20 °C

3.1: triethylamine / dichloromethane / 2 h / 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / Inert atmosphere; Reflux

5.1: N-Methyldicyclohexylamine / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 2.02 h / 20 - 160 °C / Microwave irradiation; Inert atmosphere

6.1: ozone / dimethylsulfide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; N-Methyldicyclohexylamine; ozone; triethylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; bis(tri-t-butylphosphine)palladium⁽⁰⁾; dimethylsulfide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 4.1: Grubbs' metathesis conditions / 5.1: Heck Reaction;