Technology Process of 3-((3R,9aS)-8-((R)-5-( 1H-tetrazol-1-yl)-2,3-dihydro-1H-indene-1-carbonyl)octahydropyrazino[2,1-c][1,4]oxazin-3-yl)-6-fluoro-2-methylbenzonitrile
There total 16 articles about 3-((3R,9aS)-8-((R)-5-( 1H-tetrazol-1-yl)-2,3-dihydro-1H-indene-1-carbonyl)octahydropyrazino[2,1-c][1,4]oxazin-3-yl)-6-fluoro-2-methylbenzonitrile which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 20 - 100 °C
1.2: 0.75 h / 0 - 5 °C
2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
3.1: triethylamine; trifluoroacetic acid / dichloromethane / 24 h / 20 °C
3.2: 2 h / 20 °C
4.1: 1 h / 20 °C
5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 3 h / 20 °C
6.1: Chiralcel OD / methanol; acetonitrile; carbon dioxide / 35 °C / 75007.5 Torr / Supercritical conditions; liquid CO2
With
bis(triphenylphosphine)palladium(II) chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; carbon dioxide; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
2.1: bis(triphenylphosphine)palladium(II) chloride / 1,4-dioxane / 22 h / 20 - 100 °C
2.2: 0.75 h / 0 - 5 °C
3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C
4.1: triethylamine; trifluoroacetic acid / dichloromethane / 24 h / 20 °C
4.2: 2 h / 20 °C
5.1: 1 h / 20 °C
6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 3 h / 20 °C
7.1: Chiralcel OD / methanol; acetonitrile; carbon dioxide / 35 °C / 75007.5 Torr / Supercritical conditions; liquid CO2
With
N-Bromosuccinimide; bis(triphenylphosphine)palladium(II) chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; trifluorormethanesulfonic acid; carbon dioxide; acetonitrile;
- Guidance literature:
-
Multi-step reaction with 10 steps
1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere
2: N-Bromosuccinimide / trifluorormethanesulfonic acid / 1 h / 0 - 20 °C
3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / ethanol / 4 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 72 h / 0 - 20 °C
5: ethanol / 0.5 h / 150 °C / Microwave irradiation
6: cyanomethylenetributyl-phosphorane / benzene / 16 h / 100 °C
7: Chiralpak AD / n-heptane; isopropyl alcohol
8: 1 h / 20 °C
9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 3 h / 20 °C
10: Chiralcel OD / methanol; acetonitrile; carbon dioxide / 35 °C / 75007.5 Torr / Supercritical conditions; liquid CO2
With
N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; cyanomethylenetributyl-phosphorane;
In
methanol; ethanol; n-heptane; dichloromethane; N,N-dimethyl acetamide; trifluorormethanesulfonic acid; carbon dioxide; isopropyl alcohol; acetonitrile; benzene;