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Synthetic route

methyl bromide
74-83-9

methyl bromide

Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

metandienone
72-63-9

metandienone

Conditions
ConditionsYield
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃;
Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃;
94.6%
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃;
Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃;
94.6%
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40 - 45℃;
Stage #2: Androsta-1,4-diene-3,17-dione In toluene at 50 - 55℃;
Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3;
93.8%
methylene chloride
74-87-3

methylene chloride

Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

metandienone
72-63-9

metandienone

Conditions
ConditionsYield
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃;
Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃;
92.5%
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃;
Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃;
92.5%
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 30 - 35℃;
Stage #2: Androsta-1,4-diene-3,17-dione In tetrahydrofuran at 50 - 55℃;
Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3;
92.5%
Androsta-1,4-diene-3,17-dione
897-06-3

Androsta-1,4-diene-3,17-dione

methyl iodide
74-88-4

methyl iodide

metandienone
72-63-9

metandienone

Conditions
ConditionsYield
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃;
Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃;
90.8%
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃;
Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃;
90.8%
Stage #1: methyl iodide With magnesium In diethyl ether at 30 - 35℃;
Stage #2: Androsta-1,4-diene-3,17-dione In benzene at 50 - 55℃;
Stage #3: With hydrogenchloride In water at 50 - 55℃; pH=2 - 3;
90.8%
17-methyltestosterone
58-18-4

17-methyltestosterone

metandienone
72-63-9

metandienone

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 0 - 20℃; for 48h;78%
With selenium(IV) oxide
mit Hilfe von Didymella lycopersici;
monomethyl oxalyl chloride
5781-53-3

monomethyl oxalyl chloride

metandienone
72-63-9

metandienone

methyl ((8R,9S,10R,13S,14S,17S)-10,13,17-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl) oxalate

methyl ((8R,9S,10R,13S,14S,17S)-10,13,17-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl) oxalate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;95%
metandienone
72-63-9

metandienone

(8S,9S,10R,13S,14S)-10,13,17-trimethyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3(10H)-one
64760-67-4

(8S,9S,10R,13S,14S)-10,13,17-trimethyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-3(10H)-one

Conditions
ConditionsYield
With Amberlyst-15 In dichloromethane at 20℃; for 6h;90%
metandienone
72-63-9

metandienone

A

15α,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one

15α,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one

B

6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one
33526-41-9

6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one

Conditions
ConditionsYield
With Penicillium notatum KCH 904 In water; acetone at 27℃; for 264h; Enzymatic reaction;A 83%
B 9%
di-tert-butyl-diazodicarboxylate
870-50-8

di-tert-butyl-diazodicarboxylate

metandienone
72-63-9

metandienone

C30H46N2O6

C30H46N2O6

Conditions
ConditionsYield
With cerium(III) chloride; tetrabutyl-ammonium chloride In acetonitrile for 48h; Inert atmosphere; Irradiation; diastereoselective reaction;71%
metandienone
72-63-9

metandienone

17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one
77702-25-1

17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one

Conditions
ConditionsYield
With hydrogenchloride at 60℃; for 0.5h;60%
With hydrogenchloride In methanol; water for 16h; Reflux;
metandienone
72-63-9

metandienone

androsta-3,5-dien-17β-ol, 17-methyl-

androsta-3,5-dien-17β-ol, 17-methyl-

Conditions
ConditionsYield
Stage #1: metandienone With C19H26ClIrN3O(1+)*Cl(1-) In water; acetonitrile at 80℃; for 0.166667h; Green chemistry;
Stage #2: With formic acid In water; acetonitrile at 80℃; for 4h; Green chemistry;
35%
metandienone
72-63-9

metandienone

17-methyltestosterone
58-18-4

17-methyltestosterone

Conditions
ConditionsYield
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature;34%
metandienone
72-63-9

metandienone

UDP-glucuronic acid
2616-64-0

UDP-glucuronic acid

A

17β-methyl-5β-androst-1-ene-17α-ol-3α-O-glucuronide
1062581-61-6

17β-methyl-5β-androst-1-ene-17α-ol-3α-O-glucuronide

B

17α-methyl-5β-androstane-17β-ol-3α-O-glucuronide

17α-methyl-5β-androstane-17β-ol-3α-O-glucuronide

Conditions
ConditionsYield
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4;A 25%
B n/a
metandienone
72-63-9

metandienone

A

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

B

(3aα,8aα,8bβ)-dodecahydro-5aβ,6α-dimethyl-6β-hydroxy-2'-methyl-as-indacene-3(R)-spiro-(2',5'-cyclohexadienone)

(3aα,8aα,8bβ)-dodecahydro-5aβ,6α-dimethyl-6β-hydroxy-2'-methyl-as-indacene-3(R)-spiro-(2',5'-cyclohexadienone)

Conditions
ConditionsYield
With axenic culture of strain T76 Scenedesmus quadricaudaA 11%
B 21%
With axenic culture of strain T76 of Scenedesmus quadricaudaA 11%
B 21%
metandienone
72-63-9

metandienone

anti-17α-Methyl-17β-hydroxy-Δ1,4-androstadien-3-N-chlorimin

anti-17α-Methyl-17β-hydroxy-Δ1,4-androstadien-3-N-chlorimin

Conditions
ConditionsYield
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, NH4Cl; Multistep reaction;
pyridine
110-86-1

pyridine

metandienone
72-63-9

metandienone

methandienone 17β-sulfate pyridinium salt
143579-41-3

methandienone 17β-sulfate pyridinium salt

Conditions
ConditionsYield
With chlorosulfonic acid 1.) -5 deg C, 2.) RT, 3 h; Yield given. Multistep reaction;
metandienone
72-63-9

metandienone

metanedienone-17-sulfate
119888-55-0

metanedienone-17-sulfate

Conditions
ConditionsYield
With sulfur trioxide pyridine complex In N,N-dimethyl-formamide for 12h; Ambient temperature;3.8 g
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
24589-78-4

N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide

metandienone
72-63-9

metandienone

(8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-3,17-bis-trimethylsilanyloxy-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclopenta[a]phenanthrene
136693-32-8

(8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-3,17-bis-trimethylsilanyloxy-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclopenta[a]phenanthrene

Conditions
ConditionsYield
With ammonium iodide In ethyl acetate for 1h; Heating;97 % Chromat.
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h;
With ammonium iodide; ethanethiol In acetonitrile at 80℃; for 0.5h;
metandienone
72-63-9

metandienone

3,5-Dioxo-17β-hydroxy-17α-methyl-10(5->4)-abeo-Δ1-androsten
13712-20-4

3,5-Dioxo-17β-hydroxy-17α-methyl-10(5->4)-abeo-Δ1-androsten

Conditions
ConditionsYield
(i) PhCO3H, CHCl3, (ii) (UV-irradiation), dioxane; Multistep reaction;
methanol
67-56-1

methanol

metandienone
72-63-9

metandienone

1-Hydroxy-4.17.17-trimethyl-7.8.9.11.12.15.16.17-octahydro-6H-cyclopentaphenanthren
94761-63-4

1-Hydroxy-4.17.17-trimethyl-7.8.9.11.12.15.16.17-octahydro-6H-cyclopentaphenanthren

Conditions
ConditionsYield
With hydrogenchloride
methanol
67-56-1

methanol

metandienone
72-63-9

metandienone

13-Chlor-1-methoxy-4.17.17-trimethyl-13ξ-gonatrien-(A)
96671-98-6

13-Chlor-1-methoxy-4.17.17-trimethyl-13ξ-gonatrien-(A)

Conditions
ConditionsYield
With hydrogenchloride
methanol
67-56-1

methanol

metandienone
72-63-9

metandienone

17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one
77702-25-1

17,17-dimethyl-18-norandrosta-1,4,13(14)-trien-3-one

Conditions
ConditionsYield
With hydrogenchloride
metandienone
72-63-9

metandienone

17β-Hydroxy-17α-methyl-Δ1.5-androstadien-3-on
2694-97-5

17β-Hydroxy-17α-methyl-Δ1.5-androstadien-3-on

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide
metandienone
72-63-9

metandienone

A

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

B

(3S,3aS,5aS,6R,6aR,11aS,11bS)-3,6-Dihydroxy-3,3a,6-trimethyl-1,2,3,3a,4,5,5a,6,6a,7,10,11,11a,11b-tetradecahydro-indeno[5,4-f]azulen-8-one

(3S,3aS,5aS,6R,6aR,11aS,11bS)-3,6-Dihydroxy-3,3a,6-trimethyl-1,2,3,3a,4,5,5a,6,6a,7,10,11,11a,11b-tetradecahydro-indeno[5,4-f]azulen-8-one

C

C20H28O2

C20H28O2

D

5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

Conditions
ConditionsYield
With water In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given;
metandienone
72-63-9

metandienone

A

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

1,17α-dimethyl-1,3,5(10)-estratriene-3,17β-diol

B

C20H28O2

C20H28O2

C

5β,17β-dihydroxy-17α-methyl-androst-1-en-3-one

5β,17β-dihydroxy-17α-methyl-androst-1-en-3-one

D

5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

5α,17β-dihydroxy-17α-methyl-androst-1-en-3-one

Conditions
ConditionsYield
In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given;
With water In 1,4-dioxane at 24℃; for 480h; Irradiation; green alga T76 Scenedesmus quadricauda; Yield given. Further byproducts given. Yields of byproduct given;
metandienone
72-63-9

metandienone

A

17β-hydroxy-17α-methylandrost-4-en-3β-ol
571-03-9

17β-hydroxy-17α-methylandrost-4-en-3β-ol

B

(3R,8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

(3R,8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 2h;
metandienone
72-63-9

metandienone

17α-17-hydroxy-17-methylandrosta-1,4-dien-3-one
33526-40-8

17α-17-hydroxy-17-methylandrosta-1,4-dien-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature
2: H2O / 24 h
View Scheme
metandienone
72-63-9

metandienone

17-epimetandienone,bis-TMS

17-epimetandienone,bis-TMS

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature
2: H2O / 24 h
3: trimethylsilylimidazole / 0.17 h / 60 °C
4: trimethyliodosilane / 0.25 h / 60 °C
View Scheme
metandienone
72-63-9

metandienone

(8R,9S,10R,13S,14S,17R)-10,13,17-Trimethyl-17-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
73024-97-2

(8R,9S,10R,13S,14S,17R)-10,13,17-Trimethyl-17-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3.8 g / sulfur trioxide pyridine complex / dimethylformamide / 12 h / Ambient temperature
2: H2O / 24 h
3: trimethylsilylimidazole / 0.17 h / 60 °C
View Scheme
metandienone
72-63-9

metandienone

17α-Methyl-androsta-1,5-dien-3β,17β-diol
2694-98-6

17α-Methyl-androsta-1,5-dien-3β,17β-diol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOtBu / dimethylsulfoxide
2: NaBH4 / methanol
View Scheme

Raw Materials

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