Technology Process of Methanesulfonic acid (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
There total 16 articles about Methanesulfonic acid (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester which
guide to synthetic route it.
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synthetic route:
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104419-01-4
Methanesulfonic acid (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
- Guidance literature:
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Multi-step reaction with 13 steps
1: 1.) lithium diisopropylamide; 2.) potassium carbonate / 1.) THF, -78 deg C, 1 h; 2.) DMF, 100 deg C, 2 h, 50 deg C, 10 min
2: 76 percent / thionyl chloride, pyridine / 0.17 h / 0 °C
3: 69 percent / DBU / benzene / 0.25 h / Heating
4: 92 percent / hydrogen / 5 percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr
5: 99 percent / lithium aluminum hydride / tetrahydrofuran / 0.5 h / Ambient temperature
6: triethylamine / CH2Cl2 / 0.17 h / 0 °C
7: 81 percent / lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature
8: pyridine / 4-(N,N-dimethylamino)pyridine / 6 h / Ambient temperature
9: p-toluenesulfonic acid / dioxane; H2O / 1 h / 80 °C
10: 85 percent / pyridine / 4-(N,N-dimethylamino)pyridine / 8 h / Ambient temperature
11: 97 percent / 5 percent KOH / methanol / 1 h / Heating
12: 170 mg / p-toluenesulfonic acid / 2 h / Ambient temperature
13: 186 mg / pyridine / 1 h / Ambient temperature
With
pyridine; potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
dmap; Rh/Al2O3;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1021/ja00282a034
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104419-01-4
Methanesulfonic acid (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 1.) lithium diisopropylamide; 2.) potassium carbonate / 1.) THF, -78 deg C, 1 h; 2.) DMF, 100 deg C, 2 h, 50 deg C, 10 min
2: 76 percent / thionyl chloride, pyridine / 0.17 h / 0 °C
3: 69 percent / DBU / benzene / 0.25 h / Heating
4: 92 percent / hydrogen / 5 percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr
5: 99 percent / lithium aluminum hydride / tetrahydrofuran / 0.5 h / Ambient temperature
6: triethylamine / CH2Cl2 / 0.17 h / 0 °C
7: 81 percent / lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature
8: pyridine / 4-(N,N-dimethylamino)pyridine / 6 h / Ambient temperature
9: p-toluenesulfonic acid / dioxane; H2O / 1 h / 80 °C
10: 85 percent / pyridine / 4-(N,N-dimethylamino)pyridine / 8 h / Ambient temperature
11: 97 percent / 5 percent KOH / methanol / 1 h / Heating
12: 170 mg / p-toluenesulfonic acid / 2 h / Ambient temperature
13: 186 mg / pyridine / 1 h / Ambient temperature
With
pyridine; potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
dmap; Rh/Al2O3;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1021/ja00282a034
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104419-01-4
Methanesulfonic acid (3S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4S,5S)-5-((R)-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
- Guidance literature:
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Multi-step reaction with 12 steps
1: 76 percent / thionyl chloride, pyridine / 0.17 h / 0 °C
2: 69 percent / DBU / benzene / 0.25 h / Heating
3: 92 percent / hydrogen / 5 percent rhodium on alumina / ethyl acetate / 13 h / 5320 Torr
4: 99 percent / lithium aluminum hydride / tetrahydrofuran / 0.5 h / Ambient temperature
5: triethylamine / CH2Cl2 / 0.17 h / 0 °C
6: 81 percent / lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature
7: pyridine / 4-(N,N-dimethylamino)pyridine / 6 h / Ambient temperature
8: p-toluenesulfonic acid / dioxane; H2O / 1 h / 80 °C
9: 85 percent / pyridine / 4-(N,N-dimethylamino)pyridine / 8 h / Ambient temperature
10: 97 percent / 5 percent KOH / methanol / 1 h / Heating
11: 170 mg / p-toluenesulfonic acid / 2 h / Ambient temperature
12: 186 mg / pyridine / 1 h / Ambient temperature
With
pyridine; potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
dmap; Rh/Al2O3;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1021/ja00282a034