Method and apparatus for synthesis of highly isomerically pure s

Details Method and apparatus for synthesis of highly isomerically pure s Method and apparatus for synthesis of highly isomerically pure s

1991-08-22

1993-03-16

Evans, Joseph E.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549345, 549427, 549497, 549510, 549511, 558 51, C07D30100, C07D30132

Patent

active

051946378

ABSTRACT:
Methods are provided for producing isomerically enriched camphorsulfonates, and in particular a diastereomerically enriched glycidyl camphorsulfonate by bromide-casylate exchange between an alkyl casylate and the bromide analog of the desired casylate, followed by separation of a higher melting diastereomer by selective recrystallization. There is also shown the production of a desired casylate by reacting a racemic or enantiomerically enriched arenesulfonate with a quaternary casylate. Randomization and recycling of an isomerically enriched casylate is provided by reaction with an achiral bromide analog in the presence of a quaternary salt. Specially adapted apparatus for conducting the randomization reaction is provided. There is also shown a process for producing an alkyl casylate by the reaction of a metal casylate and a quaternary casylate with a trialkyl phosphite in the presence of a slight molar excess of sulfuric acid.

REFERENCES:
patent: 3053855 (1962-09-01), Maerker et al.
patent: 3859314 (1975-01-01), Dukes et al.
patent: 4395542 (1983-07-01), Sury
patent: 4540769 (1985-09-01), Dobinson et al.
patent: 4810808 (1989-03-01), Tomita et al.
patent: 4831101 (1989-05-01), Jellinek et al.
patent: 4931576 (1990-06-01), Wirth et al.
Advertisement, Aldrich Chemical Co. J. Org. Chem., vol. 55, #19 (1990).
Aitken, Royer, and Husson, J. Org. Chem. 55:2814-2820 (1990).
Guivisdalsky, and Bittman, J. Org. Chem. 54:4643-4648 (1989).
Byun, and Bittman, Tetrahedron Letters, vol. 30, #21:2751-2754 (1989).
Hahn and Tompkins, J. Org. Chem. 53:5783-5785 (1988).
Klunder, Tetsue and Sharpless, J. Org. Chem. 54:1295-1304 (1989).
Nitta, Arakawa and Naoto, Chem. Pharm. Bull. 34:2710 (1986).
Najdi, Reichlin and Kurth, J. Org. Chem. 55:6241-6244 (1989).
Jurczak, Pikul, and Bauer, T. Tetrahedron 42,2:447-450.

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