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17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
With water; trifluoroacetic acid In tetrahydrofuran at 20℃; for 2h; | 77% |
Conditions | Yield |
---|---|
Stage #1: C25H35NO4; methyllithium In diethyl ether at 0 - 10℃; for 4h; Cooling with ice; Stage #2: With hydrogenchloride; water In acetone at 25℃; for 8h; Solvent; | 72% |
methyllithium
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Stage #1: 17α-[(±)1-(1-ethoxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene; methyllithium In diethyl ether at 0 - 10℃; for 4h; Stage #2: With hydrogenchloride In acetone at 25℃; for 8h; | 72% |
3,3-ethylenedioxy-17β-cyano-17α-chloromethyl(dimethyl)siloxy estren-5(10),9(11)diene
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
With di-t-butyl biphenyl; lithium In tetrahydrofuran at -70℃; for 2.25h; Title compound not separated from byproducts; |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / DMAP; TEA / tetrahydrofuran / 20 °C 2: Li; di-t-butyl biphenyl / tetrahydrofuran / 2.25 h / -70 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale 2.1: diethyl ether / 4 h / 0 - 10 °C / Cooling with ice 2.2: 8 h / 25 °C View Scheme |
17α-hydroxy-19-norpregna-5(10),9(11)-diene-3,20-dione 3,20-bis(ethylene acetal)
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
ethylene deltenone
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: acetic acid / methanol / 20 °C / Large scale 2.1: ethyl vinyl ether; toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling with ice; Large scale 2.2: 8 h / 0 - 10 °C / Large scale 2.3: 4 h / 25 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1.1: acetic acid / methanol / 20 °C / Large scale 2.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale 3.1: 2 h / 0 - 10 °C / Cooling with ice 3.2: 0.5 h View Scheme | |
Multi-step reaction with 3 steps 1.1: acetic acid / methanol / 20 °C / Large scale 2.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale 3.1: tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 - 10 °C / Cooling with ice 3.2: 2 h / 25 °C View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid / methanol / 20 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling; Large scale 3: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Cooling; Large scale View Scheme |
ethylene deltenone
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: acetic acid / methanol / 20 °C / Large scale 2.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale 3.1: diethyl ether / 4 h / 0 - 10 °C / Cooling with ice 3.2: 8 h / 25 °C View Scheme |
methyllithium
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Stage #1: C25H35NO4; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice; Stage #2: With hydrogenchloride; water In methanol at 25℃; for 2h; Solvent; Overall yield = 73%; Overall yield = 6.6 g; | |
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 8h; Cooling; Large scale; Overall yield = 1036 g; |
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Stage #1: C25H35NO4; methyl Grignard reagent at 0 - 10℃; for 2h; Cooling with ice; Stage #2: With hydrogenchloride; water for 0.5h; Solvent; Overall yield = 68%; Overall yield = 2.1g; |
methyllithium
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Stage #1: 17α-[(±)1-(1-n-propyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice; Stage #2: With hydrogenchloride; water In tetrahydrofuran; 2-methyltetrahydrofuran for 0.5h; Solvent; Overall yield = 70%; Overall yield = 4g; | |
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Overall yield = 70 %; Overall yield = 4.0 g; |
methyllithium
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Stage #1: 17α-[(±)1-(1-isobutyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice; Stage #2: With hydrogenchloride; water In tetrahydrofuran; 2-methyltetrahydrofuran for 0.5h; Solvent; Overall yield = 67%; Overall yield = 4.7g; | |
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Overall yield = 67 %; Overall yield = 4.7 g; |
methyllithium
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Stage #1: C26H35NO4; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice; Stage #2: With hydrogenchloride; water In tetrahydrofuran; 2-methyltetrahydrofuran for 0.5h; Solvent; Overall yield = 72%; Overall yield = 11.2 g; |
methyllithium
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Stage #1: 3,3-(ethylene-dioxy)-17β-cyano-17α-hydroxy-19-norpregna-5(10),9(11)-diene With toluene-4-sulfonic acid; ethyl vinyl ether In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Large scale; Stage #2: methyllithium In tetrahydrofuran; diethyl ether at 0 - 10℃; for 8h; Large scale; Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 25℃; for 4h; Large scale; Overall yield = 75%; Overall yield = 1036 g; | A n/a B n/a |
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale 2.1: 2 h / 0 - 10 °C / Cooling with ice 2.2: 0.5 h View Scheme | |
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale 2.1: tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 - 10 °C / Cooling with ice 2.2: 2 h / 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling; Large scale 2: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Cooling; Large scale View Scheme |
Conditions | Yield |
---|---|
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Overall yield = 72 %; Overall yield = 11.2 g; |
methyllithium
B
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Reagent/catalyst; Solvent; Overall yield = 73 %; Overall yield = 6.6 g; |
3,3-dimethoxy-estra-5(10),9(11)-diene-17-one
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide / tetrahydrofuran; acetone / 2 h / 5 - 40 °C / Inert atmosphere 1.2: 1 h / 35 - 40 °C 2.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C 3.1: sodium methylate; methanol / 3 h / 60 - 65 °C 3.2: 1 h / Heating 4.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate; methanol / 3 h / 60 - 65 °C 1.2: 1 h / Heating 2.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C View Scheme |
3,3-(2,2-dimethyltrimethylene-1,3-dioxy)-5(10),9(11)-estradien-17-one
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide / tetrahydrofuran; acetone / 2 h / 5 - 40 °C / Inert atmosphere 1.2: 1 h / 35 - 40 °C 2.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C 3.1: sodium methylate; methanol / 3 h / 60 - 65 °C 3.2: 1 h 4.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid; acetic acid at 20 - 30℃; for 0.166667h; | 59 g |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C 2.1: sodium methylate; methanol / 3 h / 60 - 65 °C 2.2: 1 h 3.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide / tetrahydrofuran; acetone / 2 h / 5 - 40 °C / Inert atmosphere 1.2: 1 h / 35 - 40 °C 2.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C 3.1: sodium methylate; methanol / 3 h / 60 - 65 °C 3.2: 1 h 4.1: hydrogenchloride / methanol; water / 0.17 h / 20 - 30 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate; methanol / 3 h / 60 - 65 °C 1.2: 1 h 2.1: hydrogenchloride / methanol; water / 0.17 h / 20 - 30 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 20 - 30℃; for 0.166667h; | 52 g |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 20 - 30℃; for 1h; | 46 g |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate; methanol / methanol / 2 h / 60 - 65 °C 1.2: 1 h / Heating 2.1: hydrogenchloride / methanol; water / 1 h / 20 - 30 °C View Scheme |
RU 3097
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C 2.1: sodium methylate; methanol / methanol / 2 h / 60 - 65 °C 2.2: 1 h / Heating 3.1: hydrogenchloride / methanol; water / 1 h / 20 - 30 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid; acetic acid at 20 - 30℃; for 0.166667h; | 51 g |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C 2.1: sodium methylate; methanol / 3 h / 60 - 65 °C 2.2: 1 h 3.1: hydrogenchloride / methanol; water / 0.17 h / 20 - 30 °C View Scheme |
ethylene glycol
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
17α-hydroxy-19-norpregna-5(10),9(11)-diene-3,20-dione 3,20-bis(ethylene acetal)
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In dichloromethane at 20℃; Inert atmosphere; | 77% |
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In dichloromethane at 18 - 25℃; for 17h; | 4.2 g |
acetic acid
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
17α-acetoxy-19-norpregna-4,9-diene-3,20-dione
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; trifluoroacetic anhydride In dichloromethane at 0℃; for 0.25h; | 62.3% |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / dichloromethane / 20 °C / Inert atmosphere 2.1: dihydrogen peroxide; Hexafluoroacetone; disodium hydrogenphosphate / dichloromethane / 0 - 5 °C 3.1: magnesium; iodine; ethylene dibromide / tetrahydrofuran / 2 h / Inert atmosphere; Heating 3.2: 1.25 h / 20 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
5α,10α-epoxy-17α-hydroxy-19-norpregn-9(11)-ene-3,20-dione 3,20-bis(ethylene acetal)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / dichloromethane / 20 °C / Inert atmosphere 2: dihydrogen peroxide; Hexafluoroacetone; disodium hydrogenphosphate / dichloromethane / 0 - 5 °C View Scheme |
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
trimethyl orthoformate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 20 - 25℃; for 3h; | 62 g |
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