2-amino-1-phenylpropanols, stereospecific synthesis thereof, and method of optically resolving the same
OwnerDaniel David Westinventor
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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.
Claims12
A stereospecific synthesis of threo isomers of 2-nitro-1-phenylpropanols having the formula ##STR11## wherein R is member selected from the group consisting of hydrogen, hydroxy, halogen, alkyl and alkoxy, x has a value of from 1 to 5 and R' is a member selected from the group consisting of hydrogen and alkyl which comprises reacting a benzaldehyde with a nitroalkane in the presence of a tertiary amine.
The process of resolving a racemic mixture of 2-amino-1 phenylpropanols having the formula ##STR12## wherein R is member selected from the group consisting of hydrogen, hydroxy, halogen, alkyl and alkoxy, x has a value of from 1 to 5, R' is member selected from the group consisting of hydrogen and alkyl and R" is member selected from the group consisting of hydrogen and alkyl and alkoxy, into its optical isomers comprising reacting said racemic mixture with a mono alkali metal salt of a tartaric ester in a biphasic hydrocarbon water system.
Dependencies are inferred from the claim text.