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13209-41-1

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Best quality with fast delivery13209-41-1
Cas No: 13209-41-1
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Pregna-1,4,9(11)-triene-3,20-dione,17,21-dihydroxy-16-methyl-, (16a)-
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Vamorolone, in stock
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Pregna-1,4,9(11)-triene-3,20-dione,17,21-dihydroxy-16-methyl-, (16a)-
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Pregna-1,4,9(11)-triene-3,20-dione,17,21-dihydroxy-16-methyl-, (16a)-
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16a-Methyl-9,11-dehydro Prednisolone
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Pregna-1,4,9(11)-triene-3,20-dione,17,21-dihydroxy-16-methyl-, (16a)-
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13209-41-1
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17.alpha.,21-Dihydroxy-16.alpha.-methylpregna-1,4,9(11)-triene-3,20-dione
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16α-Methyl-9,11-dehydro Prednisolone
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13209-41-1 Usage

Uses

A related intermediate of Prednisolone (P703740).
InChI:InChI=1/C22H28O4/c1-13-10-18-16-5-4-14-11-15(24)6-8-20(14,2)17(16)7-9-21(18,3)22(13,26)19(25)12-23/h6-8,11,13,16,18,23,26H,4-5,9-10,12H2,1-3H3/t13-,16-,18+,20+,21+,22+/m1/s1

13209-41-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 16α-Methyl-9,11-dehydro Prednisolone

1.2 Other means of identification

Product number -
Other names (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13209-41-1 SDS

13209-41-1Synthetic route

C25H36O4Si

C25H36O4Si

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
With hydrogenchloride In pentan-1-ol80%
C25H36O2Si

C25H36O2Si

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
2: hydrogenchloride / pentan-1-ol
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
37413-91-5

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,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 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
3.1: potassium carbonate; water / methanol / 0 - 20 °C
View Scheme
17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate
10106-41-9

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
With water; potassium carbonate In methanol at 0 - 20℃;
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

Methanesulfonic acid 2-((8S,10S,13S,14S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester
23776-75-2

Methanesulfonic acid 2-((8S,10S,13S,14S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

Conditions
ConditionsYield
With pyridine at 0 - 2℃; for 1.5h;85%
formaldehyd
50-00-0

formaldehyd

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one
14518-56-0

16α-methyl-17α,20;20,21-bismethylenedioxypregn-1,4,9(11)-triene-3-one

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane Ambient temperature;74%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

A

21-chloro-17α-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

21-chloro-17α-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

B

17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4,9(11)-triene-3-one

17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4,9(11)-triene-3-one

Conditions
ConditionsYield
With dmap In dichloromethane for 4h; Heating;A 69%
B 1.1%
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

A

21-chloro-17α-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

21-chloro-17α-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

B

17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4,9(11)-triene-3-one

17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4,9(11)-triene-3-one

Conditions
ConditionsYield
With dmap; methanesulfonyl chloride In dichloromethane for 4h; Heating;A 69%
B 1.1%
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

21-chloro-17α-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

21-chloro-17α-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

Conditions
ConditionsYield
With Vilsmeier reagent; water 1.) toluene, from -3 deg C to 2 deg C, 3 h, 2.) toluene, 5 deg C; Yield given. Multistep reaction;
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

21-fluoro-17α-hydroxy-16α-methyl-1,4,9(11)-ppregnatriene-3,30-dione 17-(2'-furoate)
83881-01-0

21-fluoro-17α-hydroxy-16α-methyl-1,4,9(11)-ppregnatriene-3,30-dione 17-(2'-furoate)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / pyridine / 1.5 h / 0 - 2 °C
2: 70 percent / KF / dimethylformamide / 4 h / 124 °C
3: 23 percent / 4-DMAP / CH2Cl2 / 27 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: 85 percent / pyridine / 1.5 h / 0 - 2 °C
2: 70 percent / KF / dimethylformamide / 4 h / 124 °C
3: 58 percent / 4-DMAP / CH2Cl2 / 20 h / Ambient temperature
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

9α,11β-dichloro-21-fluoro-17α-hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione 17-(2'-furoate)
83881-12-3

9α,11β-dichloro-21-fluoro-17α-hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione 17-(2'-furoate)

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / pyridine / 1.5 h / 0 - 2 °C
2: 70 percent / KF / dimethylformamide / 4 h / 124 °C
3: 23 percent / 4-DMAP / CH2Cl2 / 27 h / 40 °C
4: 72 percent / Cl2, pyridine hydrochloride / CCl4; CH2Cl2 / -35 °C
View Scheme
Multi-step reaction with 4 steps
1: 85 percent / pyridine / 1.5 h / 0 - 2 °C
2: 70 percent / KF / dimethylformamide / 4 h / 124 °C
3: 58 percent / 4-DMAP / CH2Cl2 / 20 h / Ambient temperature
4: 72 percent / Cl2, pyridine hydrochloride / CCl4; CH2Cl2 / -35 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C22H26O3
107742-74-5

C22H26O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / pyridine / 1.5 h / 0 - 2 °C
2: 17 percent / KF / dimethylformamide / 4 h / 124 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

21-fluoro-17α-hydroxy-16α-methyl-1,4,9(11)-ppregnatriene-3,30-dione
83881-00-9

21-fluoro-17α-hydroxy-16α-methyl-1,4,9(11)-ppregnatriene-3,30-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / pyridine / 1.5 h / 0 - 2 °C
2: 70 percent / KF / dimethylformamide / 4 h / 124 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

dexamethasone
50-02-2

dexamethasone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
3: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
4: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C18H24O6
88509-06-2

C18H24O6

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

des-A,B-9-keto-16α-methyl-17α,20;20,21-bismethylenedioxypregn-8α-propionic acid
88509-05-1

des-A,B-9-keto-16α-methyl-17α,20;20,21-bismethylenedioxypregn-8α-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-5(10)-en-3-one
88509-03-9

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-5(10)-en-3-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-1,3,5(10),9(11)-tetraen-3-ol
88508-99-0

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-1,3,5(10),9(11)-tetraen-3-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-1,3,5(10)-trien-3-ol 3-methyl ether
88509-01-7

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-1,3,5(10)-trien-3-ol 3-methyl ether

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-2,5(10)-dien-3-ol 3-methyl ether
88509-02-8

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-2,5(10)-dien-3-ol 3-methyl ether

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-4,9(10)-diene-3-one
88509-04-0

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-4,9(10)-diene-3-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one
1966-25-2

16α-methyl-9β,11β-oxido-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
3: 87 percent / potassium acetate / ethanol; dioxane / 19 h / Heating
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-1,3,5(10),9(11)-tetraen-3-ol 3-methyl ether
88509-00-6

16α-methyl-17α,20;20,21-bismethylenedioxy-19-norpregn-1,3,5(10),9(11)-tetraen-3-ol 3-methyl ether

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

9α-bromo-11β-hydroxy-16α-methyl-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one
88509-22-2

9α-bromo-11β-hydroxy-16α-methyl-17α,20;20,21-bismethylenedioxy-pregna-1,4-diene-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: 95 percent / 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C21(13)C3H30O5
88509-20-0

C21(13)C3H30O5

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: 1.) n-BuLi / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 4 h, then room temp., 15 h
11: sodium t-amyloxide / toluene / 0.67 h / Heating
12: 75 percent / glacial AcOH / H2O / 1.25 h / 65 °C
13: 82 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
14: LDA / tetrahydrofuran
15: sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

17 Dexamethasone-13C

17 Dexamethasone-13C

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: 1.) n-BuLi / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 4 h, then room temp., 15 h
11: sodium t-amyloxide / toluene / 0.67 h / Heating
12: 75 percent / glacial AcOH / H2O / 1.25 h / 65 °C
13: 82 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
14: LDA / tetrahydrofuran
15: sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
16: 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
17: potassium acetate / ethanol; dioxane / 19 h / Heating
18: 73 percent / 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C21(13)C3H30O6

C21(13)C3H30O6

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: 1.) n-BuLi / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 4 h, then room temp., 15 h
11: sodium t-amyloxide / toluene / 0.67 h / Heating
12: 75 percent / glacial AcOH / H2O / 1.25 h / 65 °C
13: 82 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
14: LDA / tetrahydrofuran
15: sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
16: 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
17: potassium acetate / ethanol; dioxane / 19 h / Heating
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C21(13)C3H31BrO6

C21(13)C3H31BrO6

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: 1.) n-BuLi / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 4 h, then room temp., 15 h
11: sodium t-amyloxide / toluene / 0.67 h / Heating
12: 75 percent / glacial AcOH / H2O / 1.25 h / 65 °C
13: 82 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
14: LDA / tetrahydrofuran
15: sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
16: 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

16α-methyl-17α,20;20,21-bismethylenedioxy-19-nor-3-ethylenedioxy-4,5-seco-pregna-9-ene-5-one-1,2,3

16α-methyl-17α,20;20,21-bismethylenedioxy-19-nor-3-ethylenedioxy-4,5-seco-pregna-9-ene-5-one-1,2,3

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: 1.) n-BuLi / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 4 h, then room temp., 15 h
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C18(13)C6H30O5

C18(13)C6H30O5

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: n-BuLi / tetrahydrofuran / -78 °C
11: 25 percent / sodium t-amyloxide / toluene / Heating
12: glacial AcOH / H2O / 1.25 h / 65 °C
13: 76 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
14: LDA / tetrahydrofuran
15: sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C16(13)C6H29FO5

C16(13)C6H29FO5

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: n-BuLi / tetrahydrofuran / -78 °C
11: 25 percent / sodium t-amyloxide / toluene / Heating
12: glacial AcOH / H2O / 1.25 h / 65 °C
13: 76 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
14: LDA / tetrahydrofuran
15: sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
16: 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
17: potassium acetate / ethanol; dioxane / 19 h / Heating
18: 48percent hydrofluoric acid / ethanol; tetrahydrofuran / 20 h / 0 °C
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C18(13)C6H30O6

C18(13)C6H30O6

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: n-BuLi / tetrahydrofuran / -78 °C
11: 25 percent / sodium t-amyloxide / toluene / Heating
12: glacial AcOH / H2O / 1.25 h / 65 °C
13: 76 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
14: LDA / tetrahydrofuran
15: sodium metaperiodate / tetrahydrofuran; methanol; H2O / 2.5 h / Ambient temperature
16: 0.4M perchloric acid, N-bromoacetamide / dioxane / 15 h / Ambient temperature
17: potassium acetate / ethanol; dioxane / 19 h / Heating
View Scheme
(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
13209-41-1

(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one

C18(13)C6H32O5

C18(13)C6H32O5

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 74 percent / HCl / CH2Cl2 / Ambient temperature
2: Zn / dimethylformamide; H2O / 145-147 deg C, 30 min; room temp., 2 h
3: 48 percent / Bu4NHSO4, NaOH / tetrahydrofuran; H2O / 5-10 deg C, 0.5 h, then room temp., 16 h
4: NH3, Li / tetrahydrofuran / 2 h / -78 °C
5: NH3, Li / tetrahydrofuran; ethanol
6: 1M oxalic acid / tetrahydrofuran; methanol / 2.5 h
7: 50 percent / pyridinium bromide perbromide / pyridine / room temp., 2 h 85 deg C, 1 h
8: 1.) O3; 2.) H2O2 / 1.) CH2Cl2, MeOH, acetic acid, -72 deg C, 3.5 h; 2.) water, room temp., 18 h
9: NaOAc / acetic anhydride / 2.5 h / 100 °C
10: n-BuLi / tetrahydrofuran / -78 °C
11: 25 percent / sodium t-amyloxide / toluene / Heating
12: glacial AcOH / H2O / 1.25 h / 65 °C
13: 76 percent / KO(t-butyl) / 2-methyl-propan-2-ol / 17 h / Ambient temperature
View Scheme

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