Abstract
Condensation of 2,4,5-tribenzyloxybenzaldehyde with α-cyanoacetic acid gave 2,4,5-tribenzyloxyphenyl-α-cyanoacrylic acid which on decarboxylation gave 2,4,5-tribenzyloxyphenylacrylonitrile. Stepwise reduction of the double bond with sodium amalgam and then the cyano group with diborane followed by catalytic hydrogenolysis afforded 2,4,5-trihydroxyphenylpropylamine.
Zusammenfassung
Die Kondensation von 2,4,5-Tribenzyloxybenzaldehyd mit α-Cyanessigsäure ergab 2,4,5-Tribenzyloxyphenyl-α-cyanacrylsäure; diese ergab nach Decarboxylierung 2,4,5-Tribenzyloxyphenylacrylnitril. Stufenweise Reduktion der Doppelbindung mit Natriumamalgam und dann der Cyano-Gruppe mit Diboran gefolgt von katalytischer Hydrogenolyse führte zu 2,4,5-Trihydroxyphenylpropylamin.
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References
This work was supported by the Neurosciences Research Branch, National Institute of Mental Health, Contract No. 278-0035 (ER).
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Bhat, G.A., Dickson, D.E. Synthesis of 2,4,5-trihydroxyphenylpropylamine. Monatsh Chem 115, 113–116 (1984). https://doi.org/10.1007/BF00798427
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DOI: https://doi.org/10.1007/BF00798427