Process for producing optically active β-amino alcohol

Details Process for producing optically active β-amino alcohol Process for producing optically active β-amino alcohol

2003-06-02

2008-08-05

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C564S342000, C564S343000

Reexamination Certificate

active

07408084

ABSTRACT:
A process for easily producing an optically active β-amino alcohol useful as a pharmaceutical intermediate from an inexpensive, readily available starting material is provided. A readily available α-substituted ketone is reacted with an optically active amine to yield a diastereomer mixture of an optically active α-substituted aminoketone. One of the diastereomers is isolated optionally after the diastereomers are converted to salts with an acid. The optically active α-substituted aminoketone or a salt thereof thus isolated was stereoselectively reduced to yield an optically active β-substituted amino alcohol. The optically active β-substituted amino alcohol is subjected to hydrogenolysis to produce an optically active β-amino alcohol or a salt thereof.

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Sreekumar, R. et al, “Asymmetric Synthesis of Amines by the Reductive Amination of Ketones Using (+) and (−) Norephedrine Followed by Periodated Oxidation.” Tetrahedron Asymmetry, 1993 vol. 4, No. 9, pp. 2095 to 2100, particulary, Sheme 1.

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