Conformationally defined adrenergic agents. 4. 1-(aminomethyl) phthalans: synthesis and pharmacological consequences of the phthalan ring oxygen atom

JF DeBernardis, DL Arendsen, JJ Kyncl…

Index: DeBernardis; Arendsen; Kyncl; Kerkman Journal of Medicinal Chemistry, 1987 , vol. 30, # 1 p. 178 - 184

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Citation Number: 30

Abstract

Cleavage of the methylenedioxy moiety was readily accomplished by using BBr3 in excess followed by quenching with methanol and removal of the boron as the trimethylborate/ methanol azeotrope, to yield the catecholamine hydrobromide 5. These boron tribromide cleavage reactions were done under inert atmosphere in methylene chloride at-78 OC to produce a clean conversion to the catechol.