pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Stage #1: pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate With pyridine; N-chloro-succinimide at -15℃; for 1h; Inert atmosphere; Stage #2: With sulfur dioxide at -10℃; for 0.5h; Inert atmosphere; | 98.8% |
prednisolone 21-acetate
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Stage #1: prednisolone 21-acetate With pyridine; N-chloro-succinimide at -15 - 20℃; for 0.416667h; Inert atmosphere; Stage #2: With sulfur dioxide for 1h; Inert atmosphere; | 83.5% |
prednisolone 21-acetate
A
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
B
pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate
Conditions | Yield |
---|---|
With pyridine; thionyl chloride In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Temperature; | A 50% B n/a C n/a D n/a |
21-acetoxy-pregna-4,9(11),16-triene-3,20-dinone
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
With selenium(IV) oxide; tert-butyl alcohol | |
With pyridine; selenium(IV) oxide In tert-butyl alcohol for 24h; Reflux; Inert atmosphere; | 25.27 g |
2,4,6-trimethyl-pyridine
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
prednisolon
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 1.2: 1.25 h / 5 - 20 °C 2.1: dmap / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 3h; Inert atmosphere; | 1.92 g |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 50℃; for 5h; Inert atmosphere; | 27.6 g |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
With potassium acetate; acetic acid In N,N-dimethyl-formamide at 105℃; for 5h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Large scale; | 965 g |
androsta-1,4,9(11)-triene-3,17-dione
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide / tetrahydrofuran; acetone / 2 h / 0 - 40 °C / Inert atmosphere; Large scale 1.2: 15 h / -5 - 5 °C / Large scale 2.1: dmap; triethylamine / dichloromethane / 7 h / Inert atmosphere; Reflux; Large scale 3.1: N-Bromosuccinimide / acetone; tert-butyl alcohol / 2 h / 10 - 20 °C / Large scale 3.2: 1 h / 30 - 35 °C / Inert atmosphere; Large scale 4.1: potassium acetate; acetic acid / N,N-dimethyl-formamide / 5 h / 105 °C / Inert atmosphere; Large scale View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 7 h / Inert atmosphere; Reflux; Large scale 2.1: N-Bromosuccinimide / acetone; tert-butyl alcohol / 2 h / 10 - 20 °C / Large scale 2.2: 1 h / 30 - 35 °C / Inert atmosphere; Large scale 3.1: potassium acetate; acetic acid / N,N-dimethyl-formamide / 5 h / 105 °C / Inert atmosphere; Large scale View Scheme |
androst-4,9(11)-dien-3,17-dione
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: acetone / 0.5 h / 20 °C 2.1: calcium oxide; calcium chloride; iodine / methanol; dichloromethane; water / 1.5 h / 20 °C / Inert atmosphere 3.1: potassium acetate / N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere 3.2: 0.5 h / Inert atmosphere 4.1: toluene-4-sulfonic acid; trifluoroacetic anhydride / dichloromethane / 2.5 h / 20 °C 4.2: 0.25 h 5.1: potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere 5.2: 0.5 h / Inert atmosphere 6.1: pyridine; selenium(IV) oxide / tert-butyl alcohol / 24 h / Reflux; Inert atmosphere View Scheme |
9-alpha-hydroxyandrost-4-ene-3,17-dione
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: diethyl ether / 0.5 h / 20 °C 2.1: calcium oxide; calcium chloride; iodine / methanol; dichloromethane; water / 1.5 h / 20 °C / Inert atmosphere 3.1: potassium acetate / N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere 3.2: 0.5 h / Inert atmosphere 4.1: toluene-4-sulfonic acid; trifluoroacetic anhydride / dichloromethane / 2.5 h / 20 °C 4.2: 0.25 h 5.1: potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere 5.2: 0.5 h / Inert atmosphere 6.1: pyridine; selenium(IV) oxide / tert-butyl alcohol / 24 h / Reflux; Inert atmosphere View Scheme |
17α-Hydroxy-21-iodopregna-4,9(11)-diene-3,20-dione
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium acetate / N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: toluene-4-sulfonic acid; trifluoroacetic anhydride / dichloromethane / 2.5 h / 20 °C 2.2: 0.25 h 3.1: potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere 3.2: 0.5 h / Inert atmosphere 4.1: pyridine; selenium(IV) oxide / tert-butyl alcohol / 24 h / Reflux; Inert atmosphere View Scheme |
pregna-4,9(11)-diene-3,20-dione-17-hydroxy-21-methyl
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: calcium oxide; calcium chloride; iodine / methanol; dichloromethane; water / 1.5 h / 20 °C / Inert atmosphere 2.1: potassium acetate / N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: toluene-4-sulfonic acid; trifluoroacetic anhydride / dichloromethane / 2.5 h / 20 °C 3.2: 0.25 h 4.1: potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere 4.2: 0.5 h / Inert atmosphere 5.1: pyridine; selenium(IV) oxide / tert-butyl alcohol / 24 h / Reflux; Inert atmosphere View Scheme |
anecortave
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid; trifluoroacetic anhydride / dichloromethane / 2.5 h / 20 °C 1.2: 0.25 h 2.1: potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: pyridine; selenium(IV) oxide / tert-butyl alcohol / 24 h / Reflux; Inert atmosphere View Scheme |
pregna-4,9(11)-diene-17α,21-diol-3,20-dione 17,21-diacetate
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: pyridine; selenium(IV) oxide / tert-butyl alcohol / 24 h / Reflux; Inert atmosphere View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
Stage #1: 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate; N,N-dimethyl-formamide With perchloric acid In water at 20 - 27℃; Inert atmosphere; Stage #2: With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In water; N,N-dimethyl-formamide at 20 - 35℃; Inert atmosphere; | 99% |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate
Conditions | Yield |
---|---|
Stage #1: 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate With formic acid In acetone at -5 - 0℃; for 0.0833333h; Stage #2: With potassium permanganate In water; acetone at -5 - 0℃; for 0.166667h; | 96% |
With potassium permanganate | |
With potassium permanganate; formic acid In water; acetone at -7 - -3℃; for 0.5h; Industrial scale; | 15 kg |
With potassium permanganate; oxalic acid In water; butanone at -5℃; Reagent/catalyst; Solvent; Temperature; | 50.5 g |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
Stage #1: 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate With perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In water; acetone at -10 - -5℃; for 2h; Stage #2: With potassium carbonate In water; acetone at -5 - 35℃; for 12h; | 96% |
Stage #1: 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate With perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In acetone at -10 - -5℃; Stage #2: With potassium carbonate In acetone at 33 - 37℃; | 83.36% |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Conditions | Yield |
---|---|
With potassium permanganate; formic acid In water; acetone at -5 - 0℃; for 0.5h; Solvent; Temperature; Inert atmosphere; | 86% |
(phenylthio)nitromethane
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Acetic acid 2-[(8S,10S,13S,14S,16R,17S)-10,13-dimethyl-16-(nitro-phenylsulfanyl-methyl)-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; tert-butyl alcohol Yield given; |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
methyl-d3-magnesium iodide
Conditions | Yield |
---|---|
With methylmagnesium chloride; copper(II) propionate In tetrahydrofuran at -9 - -7℃; for 0.666667h; |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
<14C>methyl iodide
Conditions | Yield |
---|---|
With methylmagnesium chloride; copper(II) propionate In tetrahydrofuran at -9 - -7℃; for 0.666667h; |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
17α,21-dihydroxy-16β-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: DBU / 2-methyl-propan-2-ol; tetrahydrofuran 2: 70 percent / HOAc 3: m-chloroperbenzoic acid 5: 90 percent / Wilkinson catalyst View Scheme | |
Multi-step reaction with 5 steps 1: DBU / 2-methyl-propan-2-ol; tetrahydrofuran 2: 70 percent / HOAc 3: 57 percent / m-chloroperbenzoic acid 5: 90 percent / Wilkinson catalyst View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Acetic acid 2-((8S,10S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-16-methylene-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: DBU / 2-methyl-propan-2-ol; tetrahydrofuran 2: 70 percent / HOAc 3: m-chloroperbenzoic acid View Scheme | |
Multi-step reaction with 4 steps 1: DBU / 2-methyl-propan-2-ol; tetrahydrofuran 2: 70 percent / HOAc 3: 57 percent / m-chloroperbenzoic acid View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Acetic acid 2-[(8S,10S,13S,14S,16R,17S)-16-(bis-phenylsulfanyl-methyl)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: DBU / 2-methyl-propan-2-ol; tetrahydrofuran 2: 70 percent / HOAc View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Acetic acid 2-[(8S,10S,13S,14S,16R,17S)-16-(benzenesulfinyl-phenylsulfanyl-methyl)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: DBU / 2-methyl-propan-2-ol; tetrahydrofuran 2: 70 percent / HOAc 3: m-chloroperbenzoic acid View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
Acetic acid 2-[(8S,10S,13S,14S,16R,17S)-16-(bis-benzenesulfinyl-methyl)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: DBU / 2-methyl-propan-2-ol; tetrahydrofuran 2: 70 percent / HOAc 3: 57 percent / m-chloroperbenzoic acid View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
16α,21-diacetoxy-17-hydroxy-pregna-1,4,9(11)-triene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: KMnO4 View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
9β,11β-epoxy-21-hydroxypregna-1,4,16-triene-3,20-dione 21-acetate
Isopropenyl acetate
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
3,21-diacetyloxy-pregna-1,3,5,9(11),16-pentaene-20-one
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In water at 80℃; for 4h; |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
6α-fluoro-1,4,9,16-tetraenepregna-3,20-dione-21-acetate
Conditions | Yield |
---|---|
With Selectfluor In acetonitrile at -10 - 25℃; for 5h; |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
methylmagnesium chloride
methyl iodide
2-oxo-2-((8S,10S,13S,14S,16R,17S)-10,13,16,17-tetramethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate
Conditions | Yield |
---|---|
Stage #1: 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate; methylmagnesium chloride; copper(II) propionate In tetrahydrofuran Cooling with acetone-dry ice; Stage #2: methyl iodide In tetrahydrofuran |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
methylmagnesium chloride
1-(Trimethylsilyl)imidazole
(Z)-2-((8S,10S,13S,14S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate
Conditions | Yield |
---|---|
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(II) propionate In tetrahydrofuran; dichloromethane at -50 - -30℃; Inert atmosphere; |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(II) propionate / dichloromethane; tetrahydrofuran / -50 - -30 °C / Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: dichloromethane; tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 1.3: -50 °C / Inert atmosphere 2.1: acetic acid; peracetic acid / toluene / 0.5 h / -10 °C / Inert atmosphere View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
(8S,10S,13S,14S,16R,17S)-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(II) propionate / dichloromethane; tetrahydrofuran / -50 - -30 °C / Inert atmosphere 2: hydrogenchloride; water / ethyl acetate 3: triethylsilane / Wilkinson's catalyst / dichloromethane / 40 °C 4: potassium carbonate; water / dichloromethane; methanol / 2 h / 5 °C / Inert atmosphere; Cooling with ice View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
16α-methyl-21-hydroxypregna-1,4,9(11)-triene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(II) propionate / dichloromethane; tetrahydrofuran / -50 - -30 °C / Inert atmosphere 2: hydrogenchloride; water / ethyl acetate 3: potassium carbonate; water / dichloromethane; methanol / 2 h / 5 °C / Inert atmosphere; Cooling with ice View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
2-oxo-2-((8S,10S,13S,14S,16R,17S)-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)ethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(II) propionate / dichloromethane; tetrahydrofuran / -50 - -30 °C / Inert atmosphere 2: hydrogenchloride; water / ethyl acetate View Scheme |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
2-oxo-2-((8S,10S,13S,14S,16R,17S)-10,13,16-trimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(II) propionate / dichloromethane; tetrahydrofuran / -50 - -30 °C / Inert atmosphere 2: hydrogenchloride; water / ethyl acetate 3: triethylsilane / Wilkinson's catalyst / dichloromethane / 40 °C View Scheme |
chloro-trimethyl-silane
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
methylmagnesium chloride
Conditions | Yield |
---|---|
Stage #1: methylmagnesium chloride With copper dichloride In tetrahydrofuran at 3℃; for 0.0166667h; Inert atmosphere; Stage #2: 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate In tetrahydrofuran at 3℃; for 0.0333333h; Grignard Reaction; Inert atmosphere; Stage #3: chloro-trimethyl-silane; methylmagnesium chloride In tetrahydrofuran at 2℃; for 0.2h; Inert atmosphere; |
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: perchloric acid / water / 20 - 27 °C / Inert atmosphere 1.2: 20 - 35 °C / Inert atmosphere 2.1: potassium carbonate / water; acetone / 40 - 46 °C / Inert atmosphere 3.1: copper dichloride / tetrahydrofuran / 0.02 h / 3 °C / Inert atmosphere 3.2: 0.03 h / 3 °C / Inert atmosphere 3.3: 1.75 h / 2.5 °C / Inert atmosphere 4.1: peracetic acid; acetic acid / dichloromethane / 18 h / 4 - 20 °C / Inert atmosphere View Scheme |
Molecule structure of Pregna-1,4,9(11),16-tetraene-3,20-dione,21-(acetyloxy)- (CAS NO.37413-91-5):
Molecular Formula: C23H26O4
Molecular Weight: 366.46 g/mol
Index of Refraction: 1.585
Molar Refractivity: 101.394 cm3
Molar Volume: 302.712 cm3
Surface Tension: 48.058 dyne/cm
Density: 1.211 g/cm3
Flash Point: 233.008 °C
Enthalpy of Vaporization: 81.081 kJ/mol
Boiling Point: 534.568 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
EINECS of Pregna-1,4,9(11),16-tetraene-3,20-dione,21-(acetyloxy)- (CAS NO.37413-91-5): 253-497-3
Pregna-1,4,9(11),16-tetraene-3,20-dione,21-(acetyloxy)- (CAS NO.37413-91-5) is used for dexamethasone, betamethasone, triamcinolone intermediate.
Pregna-1,4,9(11),16-tetraene-3,20-dione,21-(acetyloxy)- (CAS NO.37413-91-5) is also named as 21-Hydroxypregna-1,4,9(11),16-tetraene-3,20-dione 21-acetate ; 3,20-dioxopregna-1,4,9(11),16-tetraen-21-yl acetate ; Pregna-1,4,9(11),16-tetraen-21-ol-3,20-dione 21-acetate ; 21-Acetoxypregna-1,4,9(11),16-tetrene-3,20-dione ; 3,20-Dioxopregna-1,4,9(11),16-tetrene-21-ol acetate .
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