Synthesis of β‐Phenylethylamine derivatives VIII: Four diastereoisomers of 1‐(4′‐hydroxyphenyl)‐2‐(1″‐methyl‐3″‐phenylpropylamino)propanol

<jats:title>Abstract</jats:title><jats:p><jats:list list-type="explicit-label"><jats:list-item><jats:p>The two racemic‐ and the four diastereoisomeric erythro forms of the aminoalcohol II were prepared and characterized</jats:p><jats:p><jats:chem-struct-wrap><jats:chem-struct><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/gif" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/must001.gif"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:chem-struct></jats:chem-struct-wrap></jats:p></jats:list-item><jats:list-item><jats:p>The relative configurations were established by synthesizing the diastereoisomers of II from the enantiomers of<jats:italic>erythro</jats:italic>‐p‐hydroxynorephedrine and from those of 1 ‐methyl‐3‐phenylpropylamine.</jats:p></jats:list-item><jats:list-item><jats:p>The absolute configurations of the enantiomers of 1 ‐methyl‐3‐phenylpropylamine were determined by correlation with those of 2‐amino‐4‐phenylbutyric acid, of which the confuguration was known.</jats:p></jats:list-item><jats:list-item><jats:p>On the basis of these experiments the configurations of the four erythro forms can be given as follows:</jats:p><jats:p>(+)‐erythro‐II = αS : βR : γR</jats:p><jats:p>(−)‐erythro‐II = αR : βS : γS</jats:p><jats:p>(+)‐alloerythro‐II = αS : βR:γS</jats:p><jats:p>(−)‐alloerythro‐II = αR : βS : γR</jats:p></jats:list-item><jats:list-item><jats:p>Biological experiments confirmed these configurations.</jats:p></jats:list-item></jats:list></jats:p>