Method for the preparation of erythro vicinyl amino-alcohols

Details Method for the preparation of erythro vicinyl amino-alcohols Method for the preparation of erythro vicinyl amino-alcohols

1994-06-07

1995-12-19

Raymond, Richard L.

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

Organic compounds

Amino nitrogen containing

564276, 564357, 564363, C07C20952

Patent

active

RE0351288

ABSTRACT:
The present invention is concerned with the preparation of erythro N-substituted vicinal aminoalcohol derivatives from hydroxyl-protected cyanohydrin derivatives by successive Grignard reaction, transimination using a primary amine, reduction of the resulting imine and removal of the hydroxyl-protecting group. The products are obtained either as a racemate or in an optically pure form, depending upon the stereochemical composition of the cyanohydrin derivatives.

REFERENCES:
Tetrahedron Letters, vol. 31, No. 10, 1990. pp. 1447-1550; W. R. Jackson et al: "Stereoselective Syntheses of Ephedrine . . . ".
Synthesis, No. 4, Apr. 1986, pp. 301-303; L. R. Krepski et al, "A New Synthesis of 2-Aminoalcohols from O-Trimethylsilyl . . . ".
Tetrahedron Synthesis, vol. 1, No. 3, Mar. 1990, pp. 163-166, Brussee et al, "Magnesium Ion Mediated Stereospecific . . . ".

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