Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1999-05-24
2000-02-22
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564326, 564356, 564344, 544 97, C07C21300
Patent
active
06028224&
ABSTRACT:
A synthesis of fluoxetine is disclosed. The process begins with a lower alkyl ester of 3-benzoylpropionic acid, which is reduced in the presence of a chiral ligand to produce the corresponding .gamma.-hydroxy ester, and the ester is cleaved. The free acid is then condensed with the alcohol to form a .gamma.-lactone, which is treated with ammonia to provide the .gamma.-hydroxy amide. The amide undergoes a Hoffman rearrangement to provide a 2-oxo-1,3 oxazine, which is reduced to 3-(methylamino)-1-phenyl-1-propanol. The alcohol is deprotonated and reacted with a 4-chloro- or 4-fluoro benzotrifluoride to provide fluoxetine free base.
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Hilborn James Wallace
Jurgens Alex Roger
Senanayake Chris Hugh
Geist Gary
Sepracor Inc.
Vollano Jean F
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