Process for preparation of the pharmaceutically desired (S)-oxet

Details Process for preparation of the pharmaceutically desired (S)-oxet Process for preparation of the pharmaceutically desired (S)-oxet

1994-12-16

1999-03-30

Raymond, Richard L.

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

Organic compounds

Amino nitrogen containing

564302, 564347, C07C20988

Patent

active

058891862

ABSTRACT:
Improved processes for preparation of the (S)-oxetines in high enantiomeric purity centers on resolution using simulated moving bed chromatography of a racemic precursor early in the oxetine synthesis. Resolution is effected with high enantiomeric purity, and subsequent reactions of the desired enantiomer performed with high optical specificity to maintain enantiomeric purity. The undesired enantiomer may be racemized and recycled to the resolution phase to avoid undesired losses.

REFERENCES:
patent: 2985589 (1961-05-01), Broughton et al.
patent: 5104899 (1992-04-01), Young et al.
Skrebnik, Ramachandran & Brown, J. Org. Chem., 53, 2916, 1988.
Gao & Sharpless, J. Org. Chem., 53, 4081, 1988.
E. J. Corey and G. A. Reichard, Tetrahedron Letters, 30, No. 39, 5207 (1989).
Schneider and Goergens, Tetrahedron: Asymmetry, No. 4, 525, 1992.

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