Optical resolution of benzoxazines

Details Optical resolution of benzoxazines Optical resolution of benzoxazines

1988-08-03

1989-11-14

Raymond, Richard L.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C07D26536

Patent

active

048809268

ABSTRACT:
The invention relates to a process for producing a (.+-.)-3-alkyl-3,4-dihydro-2H-[1,4]benzoxazine derivate of formula (II) by stepwise racemization procedure. ##STR1## The invention further provides a process for optical resolution through the formation of a salt between a (.+-.)-benzoxazine compound and an optically active form of camphor-10-sulfonic acid. Without requiring the conventional expensive resolution reagents, this process not only assures production of an optically active isomer of compound (II) in high purity but also permits reuse of the optical resolution reagent.

REFERENCES:
patent: 2381935 (1945-08-01), Strain et al.
Monatshefte Fur Chemie, vol. 110, No. 2, pp. 257-265 (1979).
Reagents for Organic Synthesis, L. F. Fieser et al., vol. 1, pp. 108-109 (1967).
Houben-Weyl, Methoden Der Organischen Chemic, vol. VI, Part 4, pp. 555-560 (1966).
Patent Abstracts of Japan, vol. 11, No. 297, p. (C-488)(2744)(Sep. 1987).
"Asymmetrical Nonbridgehead Nitrogen-XXIV"-By R. G. Kostyanowsky et al., Tetrahedron, 38 949 (1982).
"Analysis of Permeation Profiles of Drugs From Systems Containing Micelles" by K. Juni et al., Chemical Pharmaceutical Bulletin, 26, 883 (1978).

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