• Name

  METHYL 4-AZA-5ALPHA-ANDROSTA-3-ONE-17BETA-CARBOXYLATE

• EINECS 1592732-453-0
• CAS No. 73671-92-8
• Article Data6
• CAS DataBase
• Density 1.095 g/cm³
• Solubility
• Melting Point 290-295 °C
• Formula C₂₀H₃₁NO₃
• Boiling Point 471.8 °C at 760 mmHg
• Molecular Weight 333.471
• Flash Point 239.2 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 4-Aza-3-oxo-androstane-17b-carboxylic acid methyl ester;Methyl 3-oxo-4-aza-5a-androstane-17b-carboxylate;Methyl4-aza-3-oxo-androstane-17b-carboxylate;4-Azaandrostane-17-carboxylicacid, 3-oxo-, methyl ester, (5a,17b)-;1H-Indeno[5,4-f]quinoline-7-carboxylic acid,hexadecahydro-4a,6a-dimethyl-2-oxo-, methyl ester, [4aR-(4aa,4bb,6aa,7a,9ab,9ba,11ab)]-;3-Oxo-4-aza-5a-androstan-17b-carboxylic acid methyl ester;3-Oxo-4-aza-5a-androstane-17b-carboxylic acid methyl ester;1H-Indeno[5,4-f]quinoline-7-carboxylicacid, hexadecahydro-4a,6a-dimethyl-2-oxo-, methyl ester,(4aR,4bS,6aS,7S,9aS,9bS,11aR)-;
• PSA 58.89000
• LogP 3.57270

Synthetic route

3-carbonyl-4-aza-5-androstene-17β-carboxylic acid methyl ester

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; acetic acid at 20 - 80℃; under 3750.38 - 4500.45 Torr; for 12h; Inert atmosphere; Industrial scale;	94.7723%

103335-55-3

3-oxo-4-aza-5α-androstane-17β-carboxylic acid

77-76-9

2,2-dimethoxy-propane

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;
With hydrogenchloride In methanol at 20℃; for 3h; Reflux;

103335-41-7

methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In dichloromethane

20283-95-8

3,20-dioxo-4-aza-pregnan-5-ene

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 2: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 3: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme

1416955-23-1

C20H31NO3

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / methanol / 0.58 h 2: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 3: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 4: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme

73711-89-4

3,20-dioxo-4-aza-5α-pregnane

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 2: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme

57-83-0

Progesterone

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: potassium carbonate; sodium periodate; potassium permanganate / tert-butyl alcohol; water / 1 h / 50 °C 2: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / Inert atmosphere 3: ammonium acetate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 4: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 5: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 6: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 7: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme
Multi-step reaction with 7 steps 1: potassium carbonate; sodium periodate; potassium permanganate / tert-butyl alcohol; water / 1 h / 50 °C 2: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / Inert atmosphere 3: ammonia / methanol / 0.5 h / 0 - 25 °C 4: toluene-4-sulfonic acid / methanol / 0.58 h 5: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 6: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 7: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme

3510-20-1

3,5-seco-4-norpregn-5,20-dion-3-carboxylic acid

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / Inert atmosphere 2: ammonium acetate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 3: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 4: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 5: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 6: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme
Multi-step reaction with 6 steps 1: triethylamine / tetrahydrofuran / 2 h / -5 - -2 °C / Inert atmosphere 2: ammonia / methanol / 0.5 h / 0 - 25 °C 3: toluene-4-sulfonic acid / methanol / 0.58 h 4: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 5: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 6: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme

1416955-18-4

3,5-seco-4-norpregn-5,20-dioxo-3-(ethoxycarbonyl)carboxylate

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: ammonium acetate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere 2: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 3: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 4: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 5: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme
Multi-step reaction with 5 steps 1: ammonia / methanol / 0.5 h / 0 - 25 °C 2: toluene-4-sulfonic acid / methanol / 0.58 h 3: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 4: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 5: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme

3,20-dioxo-4-aza-pregnan-5α-ol

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / water; tetrahydrofuran / 1 h / -15 - 0 °C 2: hydrogen; palladium 10% on activated carbon; triethylamine / 6225.62 Torr 3: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 4: hydrogenchloride / methanol / 3 h / 20 °C / Reflux View Scheme

328-93-8

2,5-bis(trifluoromethyl)aniline

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

164656-22-8

(5α,17β)-N-[2,5-bis(trifluoromethyl)-phenyl]-3-oxo-4-aza-5-androstane-17-carboxamide

Conditions

Conditions	Yield
Stage #1: 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester With boron tribromide In dichloromethane at 25℃; for 0.333333h; Stage #2: 2,5-bis(trifluoromethyl)aniline In dichloromethane at 50℃;	93%

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

Methyl-2-iodo-3-oxo-4-aza-5-α-androstane-17β-carboxylate

Conditions

Conditions	Yield
With I2; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile	88%

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

149198-45-8

methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate

Conditions

Conditions	Yield
Stage #1: 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester With chloro-trimethyl-silane; N,N,N,N,-tetramethylethylenediamine In dichloromethane at -14 - 20℃; for 0.0833333h; Cooling with acetone-dry ice; Stage #2: With iodine In dichloromethane for 2h; Cooling with acetone-dry ice;	87%
With trimethylsilyl iodide; N,N,N,N,-tetramethylethylenediamine; iodine 1) CH2Cl2, -15 deg C, 15 min, 2) 0 deg C, 1.5 h; Yield given. Multistep reaction;
Stage #1: 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester With chloro-trimethyl-silane; N,N,N,N,-tetramethylethylenediamine In dichloromethane at -10℃; for 0.5h; Inert atmosphere; Stage #2: With iodine In dichloromethane at -10 - 0℃; for 2h;	24.8 g

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

882-33-7

diphenyldisulfane

141057-70-7

Methyl 2-phenylsulphenyl-3-oxo-4-aza-5α-androstan-17β-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	38%

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

103335-41-7

methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate

Conditions

Conditions	Yield
With bis(trimethylsilyl)trifluoroacetamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane 20 deg C, 4 h. then 110 deg C, 18 h.; Yield given;
With benzeneseleninic anhydride In chlorobenzene for 4h; Heating;	49.5 g
With 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 25 - 110℃; for 12h; Product distribution / selectivity; Inert atmosphere;

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-thioxo-hexadecahydro-indeno[5,4-f]quinoline-7-carboxylic acid methyl ester

Conditions

Conditions	Yield
With Lawessons reagent In dichloromethane for 10h; Ambient temperature; Yield given;

79-37-8

oxalyl dichloride

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

C22H29NO5

Conditions

Conditions	Yield
Stage #1: oxalyl dichloride; 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester With pyridine In dichloromethane at -45 - -35℃; for 0.166667h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; for 0.75h;

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

98319-24-5

dihydro-finasteride

Conditions

Conditions	Yield
With hydrogenchloride; n-butyllithium; tert-butylamine In tetrahydrofuran; n-heptane; water	11.2 g (99.7%)
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 50 - 55 °C 2: benzotriazol-1-ol; dicyclohexyl-carbodiimide / methanol View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

74-88-4

methyl iodide

86283-81-0

methyl-3-oxo-4-methyl-4-aza-5α-androstane-17β-carboxylate

Conditions

Conditions	Yield
With sodium chloride In N-methyl-acetamide; mineral oil

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

104239-97-6

3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide / toluene / 12 h / 25 - 110 °C / Inert atmosphere 2.1: sulfuric acid / 3 h / 20 - 30 °C 2.2: 1.5 h / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 2.2: 2 h / 50 °C View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide / toluene / 12 h / 25 - 110 °C / Inert atmosphere 2.1: sulfuric acid / 3 h / 20 - 30 °C 2.2: 1.5 h / 0 - 5 °C 3.1: thionyl chloride / dichloromethane / 0.5 h / 25 - 30 °C / Inert atmosphere View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

dutasteride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide / toluene / 12 h / 25 - 110 °C / Inert atmosphere 2.1: sulfuric acid / 3 h / 20 - 30 °C 2.2: 1.5 h / 0 - 5 °C 3.1: thionyl chloride / dichloromethane / 0.5 h / 25 - 30 °C / Inert atmosphere 4.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 25 - 30 °C 4.2: 12 h / 40 - 42 °C / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 2.2: 2 h / 50 °C 3.1: triethylamine / acetonitrile / 4 h / -7 - -5 °C / Inert atmosphere 4.1: boron trifluoride diethyl etherate / acetonitrile / 4 h / -15 - -8 °C View Scheme
Multi-step reaction with 4 steps 1.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 2.2: 2 h / 50 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.25 h / -20 °C 4.1: boron trifluoride diethyl etherate / acetonitrile / 4 h / 76 - 78 °C View Scheme
Multi-step reaction with 4 steps 1.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 2.2: 2 h / 50 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 0 °C 4.1: boron trifluoride diethyl etherate / tetrahydrofuran / 13 h / 0 - 65 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: boron tribromide / dichloromethane / 0.33 h / 25 °C 1.2: 50 °C 2.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 2.2: 0 - 5 °C / Inert atmosphere 3.1: sodium hydrogencarbonate; Oxone / water; acetone / 30 °C View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

1416955-22-0

(5α,17β)-3-oxo-4-azaandrost-1-ene-17-(ethoxycarbonyl)carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 2.2: 2 h / 50 °C 3.1: triethylamine / acetonitrile / 4 h / -7 - -5 °C / Inert atmosphere View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

1260388-53-1

C20H29NO5S

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 2.2: 2 h / 50 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.25 h / -20 °C View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

1169835-66-8

C24H35NO4

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,N,N,N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 2.2: 2 h / 50 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 0 °C View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

C25H40N2O2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 50 - 55 °C 2: benzotriazol-1-ol; dicyclohexyl-carbodiimide View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

N-phenyl-3-oxo-4-aza-5α-androstane-17β-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 50 - 55 °C 2: benzotriazol-1-ol; dicyclohexyl-carbodiimide View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

133216-45-2

(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid cyclohexylamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol / 50 - 55 °C 2: benzotriazol-1-ol; dicyclohexyl-carbodiimide 3: N,O-bis(trimethylsilyl)trifluoroacetamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 90 - 95 °C View Scheme

73671-92-8

3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester

N-phenyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol / 50 - 55 °C 2: benzotriazol-1-ol; dicyclohexyl-carbodiimide 3: N,O-bis(trimethylsilyl)trifluoroacetamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 90 - 95 °C View Scheme

Methyl-4-aza-5alpfa-androst a-3-one -17beta-carboxylate Specification