98769-69-8Relevant articles and documents
Regioselective monochloro substitution in carbohydrates and non-sugar alcohols via Mitsunobu reaction: Applications in the synthesis of reboxetine
Dar, Abdul Rouf,Aga, Mushtaq A.,Kumar, Brijesh,Yousuf, Syed Khalid,Taneja, Subhash Chandra
, p. 6195 - 6207 (2013/09/12)
A regioselective high yielding monochloro substitution (chlorohydrin formation) via Mitsunobu reaction is reported. In carbohydrates and sterically hindered non-sugars, only the primary hydroxyl group is chlorinated, whereas in the non-sugar 1,2- and 1,3-alcohols, predominantly the secondary chloride substitution occurs. The versatile methodology provides indirect access to epoxides with the retention of configuration, as against conventional Mitsunobu reaction which generates epoxides with inversion. The methodology was successfully used as a key step in the synthesis of optically active diastereoisomers of the antidepressant drug reboxetine from (R)-2,3-O- cyclohexylidene-d-glyceraldehyde in ～43% overall yields. The Royal Society of Chemistry.
Process development and scale-up for (±)-reboxetine mesylate
Henegar, Kevin E.,Ball, Cynthia T.,Horvath, Carolyn M.,Maisto, Keith D.,Mancini, Sarah E.
, p. 346 - 353 (2012/12/31)
Redevelopment of the commercial process for the synthesis of (±)-reboxetine methanesulfonate is described. An optimized and efficient process for the synthesis of (±)-reboxetine starting from cinnamyl alcohol was developed. The redeveloped process minimizes impurity formation and utilizes simplified processing to substantially improve process yield and throughput, and is suitable for the efficient synthesis of multiton quantities of reboxetine.
Configurational studies on 2-[α-(2-ethoxyphenoxy)benzyl]morpholine FCE 20124
Melloni,Della Torre,Lazzari,et al.
, p. 1393 - 1399 (2007/10/02)
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