Desogestrel 54024-22-5 Name Desogestrel Synonyms 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol copyRight Molecular Structure CAS # 54024-22-5, Desogestrel, 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol Mo
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inquiryProduct Name: Desogestrel Synonyms: 13-ethyl-11-methylene-19-dinorpregn-4-en-20-yn-17-o(17-alpha)-1;org2969;13-ethyl-11-methylene-18,19-dinor-17alpha… Certification: ISO, BRC, KOSHER, HALAL Application
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Name:Desogestrel The alias:(13-ethyl-17-ethynyl-11-methylene-1,2,3,6,7,8,9,1Chemicalbook0,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol CAS NO:54024-22-5 EINECS NO:258-929-4 Molecular formula:C22H30O Molecular weight:310.47 Product
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inquiryProduct Name: Desogestrel Synonyms: 13-ethyl-11-methylene-19-dinorpregn-4-en-20-yn-17-o(17-alpha)-1;org2969;13-ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol;DESOGESTREL;(17a)-13-Ethyl-11
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inquiry54024-22-5 DesogestrelAppearance:White powder Storage:Store in cool & dry place Package:according to customers' requirements Application:Pharmaceuticals Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(FOB or CIF or CNF ect...)or ac
desogestrel
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water Solvent; Reflux; | 96.5% |
lithium acetylide-ethylenediamine complex
11-methylene-18a-homo-estr-4-en-17-one
desogestrel
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 21h; | 89% |
11-methylene-18a-homo-estr-4-en-17-one
trimethylsilylacetylene
desogestrel
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-hexyllithium In tetrahydrofuran; hexane at -5℃; for 0.5h; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran; hexane at 0 - 5℃; for 1h; | 89% |
Conditions | Yield |
---|---|
With lithium; ethylenediamine In tetrahydrofuran at 25℃; for 2h; continuous flow of ethyne; | 85% |
Stage #1: acetylene With lithium In ethylenediamine at 20℃; for 2h; Peterson olefination; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran at 20℃; for 2h; Further stages; | 83% |
Stage #1: acetylene With N,N,N,N,-tetramethylethylenediamine; lithium for 2h; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran at 20℃; for 2h; Stage #3: With hydrogenchloride; water In tetrahydrofuran | 83% |
C24H32OS2
desogestrel
Conditions | Yield |
---|---|
With sodium In tetrahydrofuran; ammonia at -4℃; for 1h; | 58% |
lithium acetylide-ethylenediamine complex
11-methylene-18a-homo-estr-4-en-17-one
A
desogestrel
Conditions | Yield |
---|---|
In tetrahydrofuran; ethylenediamine at 10 - 20℃; for 4h; | A 0.220 g B 0.060 g |
(+)-(1S,3aS,7aS)-hexahydro-1-(tert-butyldimethylsiloxy)-7a-ethyl-5-indanone
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 80 percent / NaH, MeOH / tetrahydrofuran; hexane / 1 h / Heating 2: 1.) NaH, 2.) n-BuLi 3: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 4: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 6: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 7: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 8: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 9: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 10: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 11: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 12: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
(+)-(1S,3aS,7aS)-3a,4,7,7a-tetrahydro-1-(tert-butyldimethylsiloxy)-6-carbomethoxy-7a-ethyl-5-hydroxyindane
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 1.) NaH, 2.) n-BuLi 2: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 3: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 4: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 5: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 6: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 7: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 8: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 9: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 10: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 11: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
(+)-13β-ethyl-11-methylenegona-4-en-17β-ol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 2: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
(+)-13β-ethyl-17β-hydroxy-11-methylenegona-4-en-3-one
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 2: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 3: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 4: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
11-carbomethoxy-13-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraen-17β-ol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 2: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 3: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 4: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 5: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 6: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 7: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 8: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 9: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
(+)-13β-ethyl-3,3-ethylenedithio-11-methylenegona-4-en-17β-ol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 2: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 3: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
17β-(tert-butyldimethylsiloxy)-13-ethyl-11-methylene-3-methoxygona-1,3,5(10)-triene
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 2: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 3: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 4: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 5: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 6: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
17β-(tert-butyldimethylsiloxy)-13-ethyl-11-(hydroxymethyl)-3-methoxygona-1,3,5(10),9(11)-tetraene
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 2: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 3: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 4: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 5: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 6: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 7: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
(+)-(1S,3aS,4S,7aS)-3a,4,7,7a-tetrahydro-1-(tert-butyldimethylsiloxy)-6-carbomethoxy-7a-ethyl-5-hydroxy-4-(2-(3-methoxyphenyl)ethyl)indane
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 2: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 3: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 4: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 5: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 6: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 7: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 8: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 9: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 10: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
17β-(tert-butyldimethylsiloxy)-11-carbomethoxy-13-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraene
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 2: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 3: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 4: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 5: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 6: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 7: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 8: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 2: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 3: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 4: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 5: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme |
13β-ethyl-11-methylenegon-4-en-3,17-dione
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 2: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 4: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 5: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme | |
Multi-step reaction with 3 steps 1: 91 percent / BF3*Et2O / tetrahydrofuran / 2.75 h / Heating 2: t-BuOK / tetrahydrofuran / 2 h / -20 - -15 °C 3: 58 percent / Na / liquid ammonia; tetrahydrofuran / 1 h / -4 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: hydrogenchloride / 1,2-dimethoxyethane; 1,4-dioxane / -10 °C 1.2: 3 h / -15 - -10 °C 1.3: 0.67 h 2.1: sodium tetrahydroborate; water / ethanol / 0 - 20 °C 3.1: zinc; acetic acid / water / 12 h / 20 °C 4.1: sodium carbonate / water; tetrahydrofuran; dichloromethane / 0.17 h / 20 °C 4.2: 20 °C 5.1: ethylenediamine; lithium / tetrahydrofuran / 5 h / 30 - 50 °C View Scheme |
13-ethyl-11-methylenegon-4-ene-3,17-dione cyclic 3-(1,2-ethanediyl dithioacetal)
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 2: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 3: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 4: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme | |
Multi-step reaction with 2 steps 1: t-BuOK / tetrahydrofuran / 2 h / -20 - -15 °C 2: 58 percent / Na / liquid ammonia; tetrahydrofuran / 1 h / -4 °C View Scheme |
13β-ethyl-11α-hydroxygon-5-ene-3,17-dione
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 94 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 2: 79 percent / HC(OEt)3, p-TsOH*H2O / CH2Cl2 / 7 h / Heating 3: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C 4: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C 5: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 6: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 7: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 8: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 9: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme |
13β-ethyl-gona-5-ene-3,11,17-trione-3,17-diethylene ketal
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C 2: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C 3: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 4: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 5: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 6: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 7: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme |
18-methyl-estra-4-en-3,11,17-trione
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 79 percent / HC(OEt)3, p-TsOH*H2O / CH2Cl2 / 7 h / Heating 2: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C 3: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C 4: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 5: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 6: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 7: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 8: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme |
D-13β-Ethyl-11-methylenegon-4-en-17α-ol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 2: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme |
D-13β-Ethyl-3,3-ethylenedithio-11-methylenegon-4-ene-17α-ol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 2: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 3: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme |
D-13β-Ethyl-11β-hydroxy-11α-methylgon-5-ene-3,11-dione-3,17-diethylene ketal
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C 2: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 3: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 4: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 5: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 6: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme |
13-ethyl-gona-4-ene-11α,17β-diol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 2: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 3: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 4: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 5: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme |
18a-homo-estr-4-ene-11,17-dione
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 2: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 3: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 4: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme | |
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran; hexane / 15 - 30 °C 2: tetrahydrofuran; hexane / Reflux 3: hydrogenchloride / methanol; water / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 1.5 h / 0 - 10 °C 1.2: 1.5 h / 25 °C 2.1: n-hexyllithium / tetrahydrofuran; hexane / 0.5 h / -5 °C 2.2: 1 h / 0 - 5 °C View Scheme |
3-methoxy-18a-homo-estra-2,5(10)-diene-11α,17β-diol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 92 percent / HCl / acetone; H2O 2: boron trifluoride diethyl ether / methanol / 1 h / Ambient temperature 3: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 4: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 5: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 6: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 7: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 8: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme |
3,3-ethylenedithio-18a-homo-estr-4-ene-11α,17β-diol
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 2: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 3: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 4: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 5: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 6: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme |
11-methylene-17-<(2,2-dimethyl)propane-1,3-dioxy>-18a-homo-estr-4-ene
desogestrel
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 2: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme |
carbon monoxide
desogestrel
Conditions | Yield |
---|---|
With dimanganese decacarbonyl In toluene at 100℃; under 760.051 Torr; for 16h; Schlenk technique; Sealed tube; | 86% |
Dimethylphenylsilane
desogestrel
Conditions | Yield |
---|---|
With potassium hydroxide In 1,2-dimethoxyethane at 45℃; for 48h; | 60% |
Conditions | Yield |
---|---|
Stage #1: desogestrel With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h; Inert atmosphere; | 58% |
desogestrel
17α-Bromethinyl-18-methyl-11-methylen-4-oestren-17β-ol
Conditions | Yield |
---|---|
With N-Bromosuccinimide; silver nitrate In acetone for 0.75h; Ambient temperature; | 51% |
acetic anhydride
desogestrel
Acetic acid (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
Conditions | Yield |
---|---|
With perchloric acid In toluene for 1h; Ambient temperature; |
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