Sorbinil by optical resolution with aminopinane derivatives

C - Chemistry – Metallurgy – 07 – D

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260/305.3

C07D 491/107 (2006.01) C07D 311/22 (2006.01) C07D 491/10 (2006.01)

Patent

CA 1202310

ABSTRACT OF THE DISCLOSURE Sorbinil is obtained in novel manner by optical resolution of racemic 2,3-dihydrospiro-6-fluoro[4H-l-benzopyran-4,4'-imidazolidine]-2',5'- dione either (a) by direct resolution via the (-)-3-aminomethylpinane salt of sorbinil or (b) by a double resolving agent technique via a mother liquor concentrate of either the (+)-3-amino-methylpinane or the (-)-2-amino-2- norpinane salt of sorbinil, followed by the quinine salt of sorbinil. The novel process gives good yields of sorbinil with lower solvent volumes and without the use of a highly toxic resolving agent. Sorbinil has the following formula: Image (I)

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