Technology Process of (E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-methylene-18-oxo-18-methoxy-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate
There total 13 articles about (E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-methylene-18-oxo-18-methoxy-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate 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:
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129708-78-7
(E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-methylene-18-oxo-18-methoxy-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate
- Guidance literature:
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Multi-step reaction with 12 steps
1: 95 percent / sodium borohydride / methanol / 1 h / 25 °C
2: 67 percent / benzene; dioxane / 24 h / Heating
3: chlorotrimethylsilane / 25 °C
4: 72 percent / NaH, MeOH / toluene / 16 h / Heating
5: 99 percent / HOAc, H2SO4 / H2O / 72 h / Heating
6: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature
7: 60 percent / K2CO3 / ethanol; toluene / 12 h / Ambient temperature
8: 82 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature
9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to -30 deg C
10: 91 percent / lithium tetrafluoroborate / tetrahydrofuran; acetonitrile / 72 h / Heating
11: 71 percent / pyrrolidine, trifluoroacetic acid / benzene / 19 h / Heating
12: 1.) titanocene dichloride / 1.) toluene, RT, 3 d, 2.) THF, RT, 40 min
With
pyrrolidine; methanol; sodium tetrahydroborate; lithium tetrafluoroborate; n-butyllithium; chloro-trimethyl-silane; formic acid; titanocene dichloride; sulfuric acid; sodium hydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1021/ja00169a033
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129708-78-7
(E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-methylene-18-oxo-18-methoxy-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate
- Guidance literature:
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Multi-step reaction with 7 steps
1: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature
2: 60 percent / K2CO3 / ethanol; toluene / 12 h / Ambient temperature
3: 82 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature
4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to -30 deg C
5: 91 percent / lithium tetrafluoroborate / tetrahydrofuran; acetonitrile / 72 h / Heating
6: 71 percent / pyrrolidine, trifluoroacetic acid / benzene / 19 h / Heating
7: 1.) titanocene dichloride / 1.) toluene, RT, 3 d, 2.) THF, RT, 40 min
With
pyrrolidine; lithium tetrafluoroborate; n-butyllithium; formic acid; titanocene dichloride; potassium carbonate; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1021/ja00169a033
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129708-78-7
(E)-(2S,6R,12bR)-(+)-methyl 12-benzyl-13-methylene-18-oxo-18-methoxy-1,2,3,4,5,6,7,12,12b-octahydro-2,6-methanoindolo<2,3-a>quinolizine-3-ethylidenoate
- Guidance literature:
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Multi-step reaction with 11 steps
1: 67 percent / benzene; dioxane / 24 h / Heating
2: chlorotrimethylsilane / 25 °C
3: 72 percent / NaH, MeOH / toluene / 16 h / Heating
4: 99 percent / HOAc, H2SO4 / H2O / 72 h / Heating
5: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature
6: 60 percent / K2CO3 / ethanol; toluene / 12 h / Ambient temperature
7: 82 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature
8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) from -78 deg C to -30 deg C
9: 91 percent / lithium tetrafluoroborate / tetrahydrofuran; acetonitrile / 72 h / Heating
10: 71 percent / pyrrolidine, trifluoroacetic acid / benzene / 19 h / Heating
11: 1.) titanocene dichloride / 1.) toluene, RT, 3 d, 2.) THF, RT, 40 min
With
pyrrolidine; methanol; lithium tetrafluoroborate; n-butyllithium; chloro-trimethyl-silane; formic acid; titanocene dichloride; sulfuric acid; sodium hydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1021/ja00169a033
