Fluoxetine process from benzoylacetonitrile

Details Fluoxetine process from benzoylacetonitrile Fluoxetine process from benzoylacetonitrile

1998-08-03

2000-02-15

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

564351, 564348, C07C26100, C07C21300

Patent

active

06025517&

ABSTRACT:
A synthesis of fluoxetine is disclosed. The process begins with benzoylacetonitrile, which is reduced, optionally in the presence of a chiral ligand, to produce the corresponding aminoalcohol, and the amine is carbamoylated without isolation. The alcohol is deprotonated and reacted with 4-chloro- or 4-fluoro benzotrifluoride or with 4-trifluoromethylphenol to provide a carbamate of fluoxetine. The carbamate is reduced with a hydride or with borane to provide fluoxetine free base. The process may be employed for the synthesis of individual enantiomers of fluoxetine.

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