Production of fluoxetine and new intermediates

Details Production of fluoxetine and new intermediates Production of fluoxetine and new intermediates

1992-08-18

1993-07-06

Raymond, Richard L.

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

Organic compounds

Carbonate esters

564347, C07C20908, C07C27122

Patent

active

052255859

ABSTRACT:
4-methyl-3-[(4-trifluormethyl)phenoxy]-3-phenyl propylamine (I) is prepared by reacting 3-dimethylamino-1-phenyl-1-propanol (III) with haloformate (VIII) to obtain a substituted propyl carbamate (IX) which is hydrolyzed under basic conditions to yield methylamino-1-phenyl-1-propanol (X). The methylamino-1-phenyl-1-propanol is then converted to fluoxetine (I) by reaction with 4-halobenzotrifluoride (XI).
In the process certain substituted carbamates are obtained as intermediates.

REFERENCES:
patent: 4018895 (1977-04-01), Molloy et al.
patent: 4194009 (1980-03-01), Molloy et al.
patent: 4199004 (1980-04-01), Wada et al.
patent: 4314081 (1982-02-01), Molloy et al.
"Synthesis of .sup.14 C- and .sup.3 H-Labeled Fluoxetine, A Selective Serotonin Uptake Inhibitor", Robertson et al., Journal Compounds and Radiopharmaceuticals, vol. XXIV, No. 11, pp. 1397-1404, Lilly Research Laboratories, Feb. 1987.
"Chiral Synthesis Via Organoboranes. 18. Selective Reductions. 43. Diisopinocampheylchloroborane as an Excellent Chiral Reducing Reagent for the Synthesis of Halo Alcohols of High Enantiomeric Purity. A Highly Enantioselective Synthesis of Both Optical Isomers of Tomoxetine, Fluoxetine, and Nisoxetine", Srebnik et al., J. Org. Chem., 1988, 53, pp. 2916-2920, 1988.

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