Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1996-08-19
1998-05-26
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568812, 549518, C07C 2974
Patent
active
057568626
ABSTRACT:
A process for producing optically active 2-halo-1-(substituted phenyl)ethanol of a formula (Ia) or optically active styrene oxide of a formula (Ib). The process comprises the steps of reacting a compound of a formula (II) with phthalic anhydride to give a compound of a formula (III), performing optical resolution on the resulting compound using an optically active organic amine as a resolving agent, and finally performing hydrolysis or alcoholysis on the optically resolved compound (Ia) or (Ib). The scheme of the above process is: ##STR1## wherein X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 haloalkyl group or a C.sub.1 -C.sub.6 haloalkoxy group, Z represents a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 alkyl group, n is 0 or an integer of 1 to 3 and m is 0 or an integer of 1 to 2. The resulting optically active compounds are useful as an intermediate for medicines.
REFERENCES:
patent: 3879476 (1975-04-01), Deli et al.
patent: 4857468 (1989-08-01), Kutsuki et al.
patent: 4996158 (1991-02-01), Oda et al.
patent: 5266485 (1993-11-01), Sawa et al.
Hartgerink, J.W. "Photochemically Initiated Reactions of Substituted 1,3-dioxolanes and 1,3-oxathiolanes in CFC13" Tetrahedron, vol. 27, pp. 4323-4334, 1971.
Hartgerink, J.W., et al., "Photochemically initiated reactions of substituted 1,3-dioxolanes and 1,3-oxathiolanes in CFCl.sub.3," Tetrahedron, vol. 27, pp. 4323-4334 (1971).
Organic Reactions, vol. II, Chapter 9, A.W. Ingersoll "The Resolution of
J. Org. Chem, American Chemical Society, 1992, 57, "The Osmium-Catalyzed Asymmetric Dihydroxylation: A New Ligand Class and a Process Improvement", K.B. Sharpless et al., pp. 2768-2771.
Kagaku Sousetsu, No. 6, "Separation of optical isomers", p. 8, Nippon Kagakukai, 1989.
Modern Synthetic Methods, vol. 5, pp. 115-198 (1989).
Kodama Hiroki
Motokawa Takuya
Yamaguchi Hiroshi
Yoshida Masanori
Ivy C. Warren
Nihon Nohyaku Co. Ltd.
Smith Lyman H.
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