Technology Process of (1-{2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl}-1H-1,2,3-triazol-4-yl)methyl methanesulfonate
There total 12 articles about (1-{2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl}-1H-1,2,3-triazol-4-yl)methyl methanesulfonate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: trichlorophosphate / 20 °C / Cooling with ice
1.2: 3 h / 50 °C
2.1: toluene / 7 h / 100 °C
3.1: sodium tetrahydroborate / methanol / 1 h / 20 °C
4.1: trifluoroacetic acid / dichloromethane / 8 h / 20 °C
5.1: CHIRALCEL OD column / hexane; isopropyl alcohol / Resolution of racemate
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C
7.1: triethylamine / dichloromethane / 3 h / 0 °C
8.1: sodium azide / water; N,N-dimethyl-formamide / 6 h / 80 °C
9.1: toluene / Reflux
10.1: potassium carbonate / tetrahydrofuran; methanol; water / 20 °C / Heating
11.1: lithium aluminium tetrahydride / tetrahydrofuran / Cooling with ice
12.1: triethylamine / dichloromethane / Cooling with ice
With
sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; potassium carbonate; triethylamine; trifluoroacetic acid; trichlorophosphate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
1.1: Vilsmeier reaction / 1.2: Vilsmeier reaction / 2.1: Wittig reaction / 4.1: Michael reaction;
DOI:10.1016/j.bmc.2012.02.054
- Guidance literature:
-
Multi-step reaction with 11 steps
1: toluene / 7 h / 100 °C
2: sodium tetrahydroborate / methanol / 1 h / 20 °C
3: trifluoroacetic acid / dichloromethane / 8 h / 20 °C
4: CHIRALCEL OD column / hexane; isopropyl alcohol / Resolution of racemate
5: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C
6: triethylamine / dichloromethane / 3 h / 0 °C
7: sodium azide / water; N,N-dimethyl-formamide / 6 h / 80 °C
8: toluene / Reflux
9: potassium carbonate / tetrahydrofuran; methanol; water / 20 °C / Heating
10: lithium aluminium tetrahydride / tetrahydrofuran / Cooling with ice
11: triethylamine / dichloromethane / Cooling with ice
With
sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; potassium carbonate; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
1: Wittig reaction / 3: Michael reaction;
DOI:10.1016/j.bmc.2012.02.054