Preparation and use of 2-methyl-5-phenylisoxazolidine

Details Preparation and use of 2-methyl-5-phenylisoxazolidine Preparation and use of 2-methyl-5-phenylisoxazolidine

1998-03-23

1999-06-29

McKane, Joseph K.

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

Organic compounds

Amino nitrogen containing

564355, C07C21308

Patent

active

059170913

ABSTRACT:
(a) An alkali metal base (hydroxide, oxide, carbonate, bicarbonate or sesquicarbonate), an acid addition salt of N-methylhydroxylamine, and (iii) water are mixed together to form a reaction mixture in which the acid of the acid addition salt has been neutralized. (b) Reaction mixture from (a) and formaldehyde or formalin are mixed together and the resultant mixture is subjected to reaction conditions that produce a reaction mixture in which N-methylnitrone has been formed. (c) Reaction mixture from (b) and styrene are mixed and the resultant mixture to subjected to reaction conditions that produce a reaction mixture in which 2-methyl-5-phenylisoxazolidine has been formed. Preferably, 2-methyl-5-phenylisoxazolidine formed in (c) is hydrogenated such that N-methyl-3-phenyl-3-hydroxypropylamine is formed, which in turn is reacted with 4-halobenzotrifluoride such that Conversion of the hydrochloride salt provides fluoxetine hydrochloride, a widely used antidepressant.

REFERENCES:
Fornefeld et al., "Cycloaddition Reaction With Methylnitrone", J. Org. Chem., 1979, vol. 44, No. 5, pp. 835-839.

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