Development of a commercial process to produce oxandrolone

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 378-388

  Cabaj, John E ^a   Kairys, David ^a   Benson, Thomas R ^a  

^a Cedarburg Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 39049125694     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op060231b     Document Type: Article

References (32)

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22. We initially isolated 4 by water knockout from DMF; however, drying of the DMF wet cake was difficult, and recrystallization from ethyl acetate/heptane was typically needed to provide adequate product purity.
23. 3 is used. Elimination of HBr in the 4-bromo regioisomer would give 11. Also, the fact that this is a kinetic effect was proven when the 4/11 ratio of a sample of 4 did not change (98/2) upon re-exposure of the enone to the reaction conditions.
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32. In particular, when a sample of the reaction mixture was heated from 25 to 100°C at 2°C/min the internal temperature did not increase over the input temperature. Also, the internal pressure did not increase higher than the background pressure caused by the boiling of the methanol solvent.