ChemicalBook CAS DataBase List Oxandrolone

Oxandrolone synthesis

8synthesis methods

Product Name:Oxandrolone
CAS Number:53-39-4
Molecular formula:C19H30O3
Molecular Weight:306.44

Oxandrolone, 17β-hydroxy-17α-methyl-2-oxa-5-androstan-3-one (29.3.10), is made by oxidation of the C1–C2 double bond of 17β-hydroxy-17α-methyl-1-androsten- 3-one by a mixture of lead tetraacetate and osmium tetroxide with an opening of the A ring of the steroid system, which forms an aldehyde acid (29.3.9). Upon reducing the aldehyde group with sodium borohydride, intramolecular cyclization takes place, directly forming a lactone (29.3.10), which is the desired oxandrolone.

(4aS,4bS,6aS,7S,9aS,9bS,11aS)-7-Hydroxy-4a,6a,7-trimethyltetradecahydroindeno[4,5-h]isochromene-2,4-dione

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Yield:53-39-4 6.1 g (75.2%)

Reaction Conditions:

with sodium borohydrid;sulfuric acid in water;N,N-dimethyl-formamide;

Steps:

4 Synthesis of 17β-Hydroxy-17α-methyl-2-oxa-5α-androstane-3-one (Reduction With Sodium Borohydride)

EXAMPLE 4 Synthesis of 17β-Hydroxy-17α-methyl-2-oxa-5α-androstane-3-one (Reduction With Sodium Borohydride) A solution of 8.5 (26.5 mmol) of 17β-hydroxy-17α-methyl-2-oxa-5α-androstane-1,3-dione in 170 ml of dimethyl formamide was cooled to 0-5° C. 1.04 g (27.5 mmol) of sodium borohydride was added to the reaction mixture in small portions over a period of 15 min keeping the temperature below 10° C. After the addition the mixture was stirred at 5-10° C. for 15 min, then checked by thin layer chromatography. After completion of the reaction 70 ml (71.4 mmol) of 10% sulfuric acid was added to the reaction mixture over a period of 15 min keeping the temperature below 20° C. After the addition of the sulfuric acid the product started to crystallize. After addition of 1000 ml of water the reaction mixture was stirred for 30 min, the precipitated crystals were filtered off, washed with water and dried at 40° C. till the weight was constant to yield 6.1 g (75.2%) of the crude title compound. M.p: 235-239° C.

References:

US6583298,2003,B1