35937-38-3

Basic information

• Product Name: 5α-17β-hydroxy-17α-methyl-Δ¹-androsten-3-one
• CAS NO: 35937-38-3
• Molecular Weight: 302.457
• Mol File: 35937-38-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 5α-17β-hydroxy-17α-methyl-Δ¹-androsten-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5α-17β-hydroxy-17α-methyl-Δ¹-androsten-3-one(35937-38-3)
• EPA Substance Registry System: 5α-17β-hydroxy-17α-methyl-Δ¹-androsten-3-one(35937-38-3)

Safety Data

• Hazardous Substances Data: 35937-38-3(Hazardous Substances Data)

Upstream product

• 74252-42-9 2-bromo-17-alpha-methyl-5-alpha-androstan-17-beta-ol-3-one 
• 304-91-6 2-iodoxybenzoic acid 
• 521-11-9 mestanolone 
• 641-82-7 ZIN⁽²²³⁾C₀₅₄₅₁ 
• 481-29-8 Epiandrosterone 
• 74252-42-9 2α-bromo-17β-hydroxy-17α-methyl-5α-androstan-3-one 

Downstream Products

• 53-39-4 oxandrolone 

Relevant articles and documents

Efficient oxidizing methods for the synthesis of oxandrolone intermediates

Mild, efficient and eco-friendly oxidation of 17α-methylandrostan- 3β-17β-diol (1) has been studied with three different reagents viz. pentavalent iodine reagent 2-iodoxy benzoic acid (IBX) in DMSO at 65°C, sodium hypochlorite and H2O2/Na2WO4 under phase transfer conditions to give 17β-hydroxy-17α- methylandrostan-3-one (mestanolone 2), a drug intermediate as oxidized product. The H2O2/Na2WO4/PTC gave mestanolone in high yield and purity whereas sodium hypochlorite/PTC system yielded some chlorinated material along with the mestanolone. However, 1 with 2.5 equivalent of IBX gave 17β-hydroxy-17α-methyl- Δ1-androsten-3- one (3) under the similar reaction conditions in good yield and single step reaction.

Preparation method of oxandrolone intermediate

The invention belongs to the technical field of organic synthesis, and provides a preparation method of 17[beta]-hydroxy-17[alpha]-methyl-1-oxo-1,2-open-loop-A-nor-5[alpha]-androstane-2-oxygen-containing carboxylic acid. The preparation method comprises the following steps: 1) mixing mestanolone, 2-iodoxybenzoic acid, a catalyst and a solvent, and then carrying out an oxidation reaction to obtain a compound 1; and 2) mixing the compound 1, an aqueous solution of an oxidizing agent, bicarbonate and acetone, and then carrying out an oxidation reaction so as to obtain the 17[beta]-hydroxy-17[alpha]-methyl-1-oxo-1,2-open-loop-A-nor-5[alpha]-androstane-2-oxygen-containing carboxylic acid. The purity of the intermediate obtained by the preparation method is greater than or equal to 98%, and the yield is 95-97%; and the preparation method disclosed by the invention is low in required reaction temperature, short in product production period, simple to operate, low in production cost, friendly to environment, and reaction time is remarkably shortened.

Development of a commercial process to produce oxandrolone

A manufacturing scale process for the preparation of the anabolic steroid Oxandrolone was developed. Key elements included the following: the bromination of methylandrostanolone with perbromide to give the 2-bromoketone in ca. 80% yield with minimal dehydration, subsequent elimination of the bromide with Li2CO3/LiBr to give the 2-enone in ca. 70% yield with minimal formation of methyltestosterone, and an ozonolysis procedure to give the penultimate intermediate in ca. 90% yield. The overall yield from methylandrostanolone to Oxandrolone using the described process was 45% as compared to the original Searle yield of 8%.