Synthesis of 2, 3, 4, 5-tetrahydro-1, 5-methano-1H-3-benzazepine via oxidative cleavage and reductive amination strategies

…, RA Singer, E Vazquez, MG Vetelino, HH Watson…

Index: Brooks, Paige R.; Caron, Stephane; Coe, Jotham W.; Ng, Karl K.; Singer, Robert A.; Vazquez, Enrique; Vetelino, Michael G.; Watson Jr., Harry H.; Whritenour, David C.; Wirtz, Michael C. Synthesis, 2004 , # 11 p. 1755 - 1758

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Citation Number: 14

Abstract

Abstract Preparations of 2, 3, 4, 5-tetrahydro-1, 5-methano-1H-3-benzazepine (5) from benzonorbornadiene (1) by oxidative cleavage and reductive amination sequences were investigated. Osmium-mediated dihydroxylation of 1 followed by NaIO 4 cleavage, reductive amination and debenzylation provides 5 in 64-73% yield overall in three operations. A tandem ozonolysis-reductive amination procedure gives 5 as the tosylate salt from ...

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