Tartaric acid monoesters of alkanolamines

Details Tartaric acid monoesters of alkanolamines Tartaric acid monoesters of alkanolamines

1983-10-17

1987-03-24

Ramsuer, Robert W.

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

Organic compounds

Carboxylic acid esters

544134, 548444, 558414, 558416, 560 20, 560 60, 560106, 560112, 560182, 564349, C07C 9304, C07C 9306, C07C 93187, C07C 9320

Patent

active

046526722

ABSTRACT:
For the analytical and preparative separation of the optical isomers of optically active alkanolamines into their optically pure antipodes a new resolution method is presented which involves an ester formation of the alkanolamines with optically pure and symmetrically O,O disubstituted (R,R)- or (S,S)-tartaric acids. The derivitization reactions are carried out in aprotic solvents and the primary and secondary functions are blocked via ion-pair formations with strong acids, e.g. dichloroacetic acid. The tartaric acid anhydrides are predominantly used as reagents but other ester formation methods are also practicable. The mixture of the diastereomeric alkanolamine tartaric acid monoesters are separable into their optically active and pure isomers by various chromotographic separation techniques, e.g. straight or reverse phase LC, but also by extraction methods e.g. Soxhlet extraction. The optically pure parent alkanolamine isomers can be obtained by ester hydrolysis, with high yield, from the optically pure fractions of the alkanolamine tartaric acid monoesters.

REFERENCES:
patent: 3337628 (1967-08-01), Crowther et al.
patent: 4039685 (1977-08-01), Koppe et al.
Newman, Optical Resolution Procedures for Chemical Compounds, vol. 3, Manhattan College, Riverdale, N.Y. (1984), pp. 7-15.
Synthetic Organic Chemicals (1932), vol. V, No. 5, Eastman Kodak Company.
The Merck Index, 9th ed., No. 7628 (1976).
Lucas, Organic Chemistry, 2nd ed., pp. 313, 314.

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