Phenyl-hydroxy-methylaminopropane

To the solution of l-phenyl-l-methoxy-2-bromopropane methylamine was added and as a result of the reaction l-phenyl-l-methoxy-2-methylaminopropane was obtained. After that l-phenyl-l-methoxy-2-methylaminopropane on hydrolysis with hydrobromic acid yielded 1-phenyl-l-hydroxy-2-methylaminopropane, i.e. racemic pseudoephedrine. The racemic base was resolved, by crystallization of their tartrates, into I- and d-pseudoephedrine. The base l-pseudoephedrine forms white rhombic crystals, melting point 118°C. The salt pseudoephedrine sulfate may be prepeared by... 

I -Ephedrine (= R, 2S)-1 -Phenyl-1 -hydroxy-2-methylaminopropane) (phenylpropanoid amino alcohol)... 

In 1921 Carl Neuberg discovered that actively growing yeast cells would convert added benzaldehyde into (R)-l-phenyl-l-hydroxy-propan-2-one. The other substrate in this asymmetric condensation reaction is acetaldehyde, which the yeast derives from its degradation of carbohydrate (see section 6.2.1.2). In 1930 this reaction was developed by Hildebrandt and Kalavehn as a key stage in the synthesis of D-ephedrine, (IR, 2S)-l-phenyl-l-hydroxy-2-methylaminopropane (Figure 6.25). ... 

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