2-amino-1-phenylpropanols, stereospecific synthesis thereof, and

Details 2-amino-1-phenylpropanols, stereospecific synthesis thereof, and 2-amino-1-phenylpropanols, stereospecific synthesis thereof, and

1997-01-08

1999-10-05

Raymond, Richard L.

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

Organic compounds

Amino nitrogen containing

549437, 549443, 564361, 564364, 568306, C07C20988

Patent

active

059627379

ABSTRACT:
Stereospecific synthesis of the racemic threo isomers of 2-nitro-1-phenylpropanols by reacting a benzaldehyde derivative with nitroalkane in the presence of a tertiary amine and reducing 2-nitro-1-phenylpropanols with, for example, lithium aluminum hydride to 2-amino-1-phenylpropanols is described. Also described are phase transfer resolution of racemic mixtures of 2-amino-1-phenylpropanol and its derivatives into their optically pure isomers by reacting a racemic mixture with the mono alkali metal salt of a tartaric acid ester in a two phase system of a hydrocarbon and water. The specification further describes therapeutically useful optically pure isomers of threo-2-amino-1-(dialkoxy or alkoxy) phenylpropanols and acid addition salts thereof.

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