Fluoxetine process from benzoylpropionic acid
US5936124A · kind A · utility
37Cited by
12References
16Claims
0Family size
Assignee
Inventors
Key dates
| Filing date | Jun 22, 1998 |
| Grant date | Aug 10, 1999 |
| Priority date | — |
| Expiry date | Jun 22, 2018 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07B2200/07
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.