Process development and scale-up for (±)-reboxetine mesylate

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 346-353

  Henegar, Kevin E ^a   Ball, Cynthia T ^a,b   Horvath, Carolyn M ^a   Maisto, Keith D ^a   Mancini, Sarah E ^a  

^a PFIZER INC   (United States)

^b Boehringer Ingelheim   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 39049103461     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op7000063     Document Type: Article

References (7)

1. Melloni, P.; Delia Torre, A.; Lazzari, E.; Mazzini, G.; Meroni, M. Tetrahedron 1985, 41, 1393-1399.
2. All compounds in this process are strictly racemic. For clarity, only a single enantiomer is shown.
3. Commercial cinnamyl alcohol was typically >99.5% trans stereoisomer. The epoxidation proceeds with complete stereospecificity.
4. The isolated diol was a single diastereomer (diastereomer <0.1%), and there was no detectable regioisomer derived from reaction of 2-ethoxyphenol at C-2 of the phenylglycidol.
5. Schneider, H. J.; Horning, R. Leibigs Ann. Chem. 1974, 1864-1871.
6. Yankee E. W.; Axen, U.; Bundy, G. L. J. Am. Chem. Soc. 1974, 5865-5876.
7. 2, also known as Red-A1, and was purchased as a 65 wt % solution in toluene.