Process for the preparation of S(+)-6-methoxy-.alpha.-methyl-2-n

Details Process for the preparation of S(+)-6-methoxy-.alpha.-methyl-2-n Process for the preparation of S(+)-6-methoxy-.alpha.-methyl-2-n

1991-07-23

1993-04-06

Dees, Jose G.

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

Organic compounds

Carboxylic acids and salts thereof

562402, 562466, C07B 5700

Patent

active

052005550

ABSTRACT:
The invention relates to a process for the preparation of S(+)-6-methoxy-.alpha.-methyl-2-naphthalene-acetic acid by resolution of R,S-6-methoxy-.alpha.-methyl-2-naphthalene-acetic acid. According to the invention R,S-6-methoxy-.alpha.-methyl-2-naphthalene-acetic acid and R(-)-2-amino-1-butanol are dissolved in water at 40.degree.-60.degree. C. Then the solution thus obtained is cooled to 25.degree.-35.degree. C. Subsequently the obtained solution is grafted with a salt of S(+)-6-methoxy-.alpha.-methyl-2-naphthalene-acetic acid and R(-)-2-amino-1-butanol, further it is cooled to 5.degree.-15.degree. C. The thereby formed crystals are separated from the solution and washed with water and subsequently hydrolyzed by adding a strong acid, whereby S(+)-6-methoxy-.alpha.-methyl-2-naphthalene-acetic acid crystallizes and the obtained crystals are separated from the mother liquor and the R(-)-6-methoxy-.alpha.-methyl-2-naphthalene-acetic acid present in the crystallization-mother liquor is racemized by heating, which racemate solution can be reused as starting material.

REFERENCES:
patent: 3686183 (1972-08-01), Dyson
patent: 4752417 (1988-06-01), Inoue et al.
patent: 4983765 (1991-01-01), Lukas et al.
patent: 5023365 (1991-06-01), Giordana et al.
Patent Abstracts of Japan, vol. 5, No. 164, Oct. 21, 1981 (C-76) (836) & JP 56/95149 (Nisshin Seifun), Aug. 1, 1981.

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