Production Method 1

63-05-8

972-46-3

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ;  12 - 16 h, 20 - 25 °C
1.2 Solvents: Pyridine ;  20 - 25 min, 25 °C; 25 °C → 0 °C; 2 - 3 h, 0 °C

Reference

Preparation of testosterone from 4-androstenedione

, China, , ,

Production Method 2

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ;  12 - 16 h, 20 - 25 °C
1.2 Reagents: Pyridine ;  neutralized

Reference

Preparation of 17β-androst-4-en-3-one-17-carboxylic acid

, China, , ,

Production Method 3

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Methanol ,  Dichloromethane ;  rt → 20 °C; 180 min, 35 °C
1.2 Reagents: Water ;  30 - 40 min
1.3 Reagents: Triethylamine ;  pH 8, 50 °C
1.4 Solvents: Water ;  50 °C → 25 °C; 2 h, 25 °C

Reference

Method for synthesis of Ethisterone

, China, , ,

Production Method 4

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: Pyridinium chloride Solvents: Ethanol ;  overnight, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  cooled

Reference

Preparation of steroidal CYP11B, CYP17, and/or CYP21 inhibitors for treating androgen-dependent conditions

, World Intellectual Property Organization, , ,

Production Method 5

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Methanol ;  3 h, rt → 40 °C

Reference

A method for preparation of 17α,21-dihydroxyprogesterone

, China, , ,

Production Method 6

63-05-8

972-46-3

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid Solvents: Ethanol ;  4 h, 40 °C
1.2 Reagents: Pyridine Solvents: Ethanol ;  pH 7, 0 °C

Reference

Method for synthesis of hydrocortisone intermediate

, China, , ,

Production Method 7

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ,  Water ;  rt → 10 °C; 0.5 h, 0 - 10 °C
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 8 - 9; 2 h, 0 - 10 °C

Reference

Green preparation of guggulsterone

, China, , ,

Production Method 8

63-05-8

972-46-3

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ;  12 - 16 h, 2025 °C
1.2 Reagents: Pyridine ;  20 - 25 min, 2025 °C → -5 °C

Reference

Method for preparing 17β-androst-4-en-3-one-17-carboxylic acid

, China, , ,

Production Method 9

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ;  12 - 16 h, 20 - 25 °C

Reference

Preparation method of Mestanolone

, China, , ,

Production Method 10

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ;  12 - 16 h, 20 - 25 °C
1.2 Reagents: Pyridine ;  20 - 25 min, neutralized

Reference

Preparation of Stanolone

, China, , ,

Production Method 11

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ;  12 - 16 h, 20 - 25 °C

Reference

Preparation of methyltestosterone from 4-androstenedione

, China, , ,

Production Method 12

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ;  12 - 16 h, 20 - 25 °C
1.2 Reagents: Pyridine ;  20 - 25 min, neutralized, 20 - 25 °C

Reference

Preparation method of 3-β-hydroxy-androstane-17-one

, China, , ,

Production Method 13

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ,  Tetrahydrofuran ;  2 h, 45 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Novel stereoselective synthesis and chromatographic evaluation of E-guggulsterone

Gioiello, Antimo; Sardella, Roccaldo; Rosatelli, Emiliano; Sadeghpour, Bahman M.; Natalini, Benedetto; et al, Steroids, 2012, 77(3), 250-254

Production Method 14

63-05-8

972-46-3

Reaction Conditions

1.1 Reagents: Triethyl orthoformate Solvents: Ethanol ;  5 min, rt
1.2 Catalysts: Methanesulfonic acid ;  30 min, rt
1.3 Reagents: Pyridine ;  5 min, rt; rt → 0 °C; 2 h, 0 °C

Reference

Optimization of the formation reaction of androstenedione ether enol

Moreno, Mayra Reyes; Ma, Yoanna; Ginarte, Alvarez; Garcia, Jose A. Ruiz; Abin, Osmell Diaz; et al, Revista CENIC, 2002, 33(3), 127-130

Production Method 15

63-05-8

972-46-3

Reaction Conditions

1.1 Reagents: Pyridine, hydrobromide (1:1) Solvents: Ethanol ;  3.5 h, 40 °C; 40 °C → rt
1.2 Reagents: Triethylamine ;  pH 7, rt

Reference

Process for preparation of Ethisterone

, China, , ,

Production Method 16

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: Pyridinium p-toluenesulfonate Solvents: Ethanol ;  4 h, 45 °C; 45 °C → 20 °C

Reference

Method for introducing side chain to the 17-position of androstenol like compound

, China, , ,

Production Method 17

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ;  rt → 40 °C; 3 h, 40 °C
1.2 Reagents: Pyridine Solvents: Ethanol ;  pH 7; 0 °C

Reference

Synthesis of intermediate of hydrocortisone of pregn-4-ene-17α,21-dihydroxy-3,20-dione-21-acetate

He, Ming-hua; Liao, Qing-jiang, Zhongguo Xinyao Zazhi, 2010, 19(3), 233-235

Production Method 18

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Ethanol ,  Tetrahydrofuran ;  1 - 2 h, 25 - 50 °C

Reference

Method for synthesis of steroid compound with 3,17-dione steroid

, China, , ,

Production Method 19

63-05-8

972-46-3

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Tetrahydrofuran ;  2 h, rt

Reference

Synthesis of spironolactone

Wang, Hongxia; Ye, Jingquan; Jiang, Zhongxing, Zhongguo Yiyao Gongye Zazhi, 2005, 36(1), 1-3

Production Method 20

571-36-8

972-46-3

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid Solvents: Ethanol ,  Tetrahydrofuran ;  20 min, rt
1.2 40 min, rt → 40 °C
1.3 Reagents: Pyridine ;  40 °C → rt

Reference

Improved synthesis of canrenone, intermediate of eplerenone

Zhang, Yinghua; Xiong, Zhigang; Qiu, Guofu; Liang, Shucai; Li, Zongtao; et al, Zhongguo Yaowu Huaxue Zazhi, 2005, 15(4), 241-243

3-Ethoxy-androsta-3,5-dien-17-one Raw materials

• Androstenedione
• Androst-5-ene-3,17-dione

3-Ethoxy-androsta-3,5-dien-17-one Preparation Products

• 3-Ethoxy-androsta-3,5-dien-17-one (972-46-3)

• 1. Evolutionary approaches in protein engineering towards biomaterial construction
  Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
• 2. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 3. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 4. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002
• 5. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544

• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Steroids and steroid derivatives Androstane steroids

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• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)