Process for the preparation of dexmethylphenidate hydrochloride

Details Process for the preparation of dexmethylphenidate hydrochloride Process for the preparation of dexmethylphenidate hydrochloride

2007-07-24

2007-07-24

Chang, Celia (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S183000, C546S237000

Reexamination Certificate

active

10793080

ABSTRACT:
The present invention provides a new and efficient process for the preparation of the dexmethylphenidate hydrochloride with high optical purity, the process comprising:(a) reacting a solution of threo-N-Boc-ritalinic acid with (S)-1-phenylethylamine, separating precipitated solid salt of (R,R)-enriched N-Boc-ritalinic acid with (S)-1-phenylethylamnine from the reaction mixture and recrystallizing, reslurring and/or trituring of said salt;(b) mixing the solid salt of (R,R)-N-Boc-ritalinic acid and (S)-1-phenylethylamine obtained in step (a) with aqueous acid and separating (R,R)-N-Boc-ritalinic acid from the mixture; and(c) reacting the (R,R)-N-Boc-ritalinic acid prepared in step (b) with hydrogen chloride and methanol to give dexmethylphenidate hydrochloride with optical purity of at least 99% ee.The present invention further provides salt of (R,R)-N-Boc-ritalinic acid with (S)-1-phenylethylamine as new intermediate in the preparation of dexmethylphenidate hydrochloride.

REFERENCES:
patent: 6441178 (2002-08-01), Zavareh et al.
Kitagawa et al. “Derivatized cyclodextrin stationary phase . . . ” CA 122:329492 (1995).

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