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7460376 
Journal Article 
A new and efficient route for the synthesis of naturally occurring catecholamines 
Bernini, R; Crisante, F; Barontini, M; Fabrizi, G 
2009 
1 
Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 
22 
3838-3842 
English 
Catecholamines, sympathomimetic drugs and adrenergic receptor antagonists, have been prepared by a regioselective oxidation of the corresponding 4-hydroxyphenethylamine derivatives by 2-iodoxybenzoic acid (IBX) in homogeneous as well as in heterogeneous conditions and followed by cleavage of the amino protective group. By using polymer-supported IBX, after the first oxidation, the oxidant can be recovered, regenerated, and efficiently reused for several additional times. An efficient, easy and green procedure for the synthesis of N-(methoxycarbonyl)dopamine, key component of many pharmaceuticals, has also been reported. © Georg Thieme Verlag Stuttgart. 
2-iodoxybenzoic acid; Aromatic hydroxylation; Catecholamines; N-(methoxycarbonyl)dopamine; Polymer-supported ibx; 2-iodoxybenzoic acid; Adrenergic receptors; Aromatic hydroxylation; Heterogeneous conditions; Key component; Naturally occurring; Polymer-supported; Protective group; Regioselective oxidation; Acids; Aromatic compounds; Brain; Hormones; Hydroxylation; Oxidation; Amines; catecholamine; methyl 3,4 dihydroxyphenethylcarbamate [n (methoxycarbonyl)dopamine; oxidizing agent; polymer; tert butyl 2 (3,4 dihydroxyphenethyl) 2 hydroxyethylcarbamate [n (tert butoxycarbonyl)norepinephrine; tert butyl 2 hydroxy 2 (4 hydroxyphenyl)ethylcarbamate [n (tert butoxycarbonyl)octopamine; tert butyl 3,4 dihydroxyphenethylcarbamate [n (tert butoxycarbonyl)dopamine; tert butyl 4 hydroxyphenethylcarbamate [n (tert butoxycarbonyl)tyramine; tert butyl [2 (3,4 dihydroxyphenyl) 2 hydroxyethyl](methyl)carbamate [n (tert butoxycarbonyl)epinephrine; tert butyl [2 hydroxy 2 (4 hydroxyphenyl)ethyl](methyl)carbamate [n (tert butoxycarbonyl)synephrine; tyramine; unclassified drug; article; deprotection reaction; drug synthesis; evaporation; hydroxylation; oxidation 
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