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

✍ Scribed by J. van Dijk; V. G. Keizer; H. D. Moed

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
686 KB
Volume
82
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The two racemic‐ and the four diastereoisomeric erythro forms of the aminoalcohol II were prepared and characterized

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The relative configurations were established by synthesizing the diastereoisomers of II from the enantiomers of erythro‐p‐hydroxynorephedrine and from those of 1 ‐methyl‐3‐phenylpropylamine.

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.

On the basis of these experiments the configurations of the four erythro forms can be given as follows:

(+)‐erythro‐II = αS : βR : γR

(−)‐erythro‐II = αR : βS : γS

(+)‐alloerythro‐II = αS : βR:γS

(−)‐alloerythro‐II = αR : βS : γR

Biological experiments confirmed these configurations.

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