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17α-acetoxy-6-methylene-19-norpregn-4-ene-3,20-dione
nomegestrol acetate
Conditions | Yield |
---|---|
With [Rh(Binap)2]+[ClO4]- In tetrahydrofuran at 80℃; for 0.5h; Solvent; Temperature; Sealed tube; Inert atmosphere; | 99% |
With palladium 10% on activated carbon; acetic acid In ethanol at 72 - 75℃; for 0.166667h; Temperature; Inert atmosphere; Large scale; | 90.2% |
With 5%-palladium/activated carbon In tetrahydrofuran; ethanol for 0.75h; Reflux; | 77% |
nomegestrol acetate
Conditions | Yield |
---|---|
With chloranil In 1,4-dioxane at 90 - 95℃; Solvent; Temperature; | 77.8% |
17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 2: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 3: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C 4: toluene-4-sulfonic acid / 24 h / 20 °C 5: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 6: trichlorophosphate / -10 °C 7: sodium tetrahydroborate / methanol / 20 °C 8: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
20,20-(ethylenedioxy)-3-methoxy-17α-hydroxy-19-norpregna-1,3,5(10)-triene
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 2: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C 3: toluene-4-sulfonic acid / 24 h / 20 °C 4: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 5: trichlorophosphate / -10 °C 6: sodium tetrahydroborate / methanol / 20 °C 7: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
17-alpha-Hydroxy-19-norprogesterone
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid / 24 h / 20 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 3: trichlorophosphate / -10 °C 4: sodium tetrahydroborate / methanol / 20 °C 5: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
Estrone
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: sodium hydroxide / acetone; water / 2 h / Reflux 2.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C 3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 4.1: sodium methylate / methanol / Reflux 4.2: 2 h / Reflux 5.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 6.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 7.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C 8.1: toluene-4-sulfonic acid / 24 h / 20 °C 9.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 10.1: trichlorophosphate / -10 °C 11.1: sodium tetrahydroborate / methanol / 20 °C 12.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
17α-acetoxy-19-norpregna-4-ene-3,20-dione
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 2: trichlorophosphate / -10 °C 3: sodium tetrahydroborate / methanol / 20 °C 4: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 2: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C 3: magnesium / chloroform; diethyl ether / 30 - 55 °C 4: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme | |
Multi-step reaction with 4 steps 1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 2: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C 3: magnesium / tetrahydrofuran / 30 - 55 °C 4: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme | |
Multi-step reaction with 4 steps 1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C 2: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C 3: magnesium / toluene / 30 - 55 °C 4: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme |
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate / -10 °C 2: sodium tetrahydroborate / methanol / 20 °C 3: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
6-formyl-3-ethoxy-17α-acetoxy-19-norpregna-3,5-diene-20-one
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 20 °C 2: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
estrone 3-methyl ether
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: sodium methylate / methanol / Reflux 3.2: 2 h / Reflux 4.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 5.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 6.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C 7.1: toluene-4-sulfonic acid / 24 h / 20 °C 8.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 9.1: trichlorophosphate / -10 °C 10.1: sodium tetrahydroborate / methanol / 20 °C 11.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C 2: toluene-4-sulfonic acid / 24 h / 20 °C 3: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 4: trichlorophosphate / -10 °C 5: sodium tetrahydroborate / methanol / 20 °C 6: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
mestranol
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: sodium methylate / methanol / Reflux 2.2: 2 h / Reflux 3.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 4.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 5.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C 6.1: toluene-4-sulfonic acid / 24 h / 20 °C 7.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 8.1: trichlorophosphate / -10 °C 9.1: sodium tetrahydroborate / methanol / 20 °C 10.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: sodium methylate / methanol / Reflux 1.2: 2 h / Reflux 2.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 3.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 4.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C 5.1: toluene-4-sulfonic acid / 24 h / 20 °C 6.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 7.1: trichlorophosphate / -10 °C 8.1: sodium tetrahydroborate / methanol / 20 °C 9.1: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme |
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C 2: magnesium / tetrahydrofuran / 30 - 55 °C 3: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C 2: magnesium / toluene / 30 - 55 °C 3: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide; dihydrogen peroxide / methanol / 20 - 25 °C 2: magnesium / chloroform; diethyl ether / 30 - 55 °C 3: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme |
nomegestrol acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / 30 - 55 °C 2: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme | |
Multi-step reaction with 2 steps 1: magnesium / toluene / 30 - 55 °C 2: chloranil / 1,4-dioxane / 90 - 95 °C View Scheme |
nomegestrol acetate
6-α-methyl-3,20-dioxo-19-norpregna-4-en-17-yl acetate
Conditions | Yield |
---|---|
With palladium 10% on activated carbon In ethanol; cyclohexane for 3h; Reflux; | 71% |
With 5%-palladium/activated carbon; cyclohexene In ethanol for 2h; Reflux; | 34% |
nomegestrol acetate
A
(3R,3aS,5aS,5bR,8'R,8aR,9R,9'S,10'R,12aR,12bS,13'S,14'S,17'R)-3,17'-diacetyl-3a,13'-dimethyl-3',8-dioxo-1',2,2',3,3',3a,4,5,5a,5b,6,7,7',8,8',8a,9',10,10',11,11',12,12',12a,12b, 13',14',15',16',17'-triacontahydro-1H-spiro[benzo[fg]cyclopenta[a]anthracene-9,6'-cyclopenta[a]phenanthrene]-3,17'-diyl diacetate
B
(3R,3aS,5aS,5bR,8'R,8aR,9S,9'S,10'R,12aR,12bS,13'S,14'S,17'R)-3,17'-diacetyl-3a,13'-dimethyl-3',8-dioxo-1',2,2',3,3',3a,4,5,5a,5b,6,7,7',8,8',8a,9',10,10',11,11',12,12',12a,12b, 13',14',15',16',17'-triacontahydro-1H-spiro[benzo[fg]cyclopenta[a]anthracene-9,6'-cyclopenta[a]phenanthrene]-3,17'-diyl diacetate
Conditions | Yield |
---|---|
In toluene for 12h; Inert atmosphere; Reflux; | A 0.41 g B 2.5 g |
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