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A recent paper reported an iridium-catalysed oxidative cyclization reaction of 4-(2-aminophenyl)butanol to give 2,3,4,5-tetrahydro-1-benzazepine in 71% yield:
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A recent paper reported an iridium-catalysed oxidative cyclization reaction of 4-(2-aminophenyl)butanol to give 2,3,4,5-tetrahydro-1-benzazepine in 71% yield: Fujita K., Yamamoto K., Yamaguchi R. Org. Lett. 4:2002;2691-2694.
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85031204736
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note
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4, filtered and evaporated. The dark oil was then subjected to column chromatography to furnish the required product.
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19
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85031202527
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note
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4, filtered and evaporated. The residue was subjected to flash column chromatography (silica gel, 20% EtOAc in pentane) to yield the required product as colourless to pale yellow oils. Microanalytically pure samples may be obtained by the precipitation of the compounds as HCl salts, recrystallised from ethanol. However, due to their low solubility in common organic solvents, the NMR spectra and subsequent reactions were carried out using the unprotonated amine.
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22
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85031199494
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note
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27N requires 85.95; H, 9.27; N, 4.77%. Found C, 85.93; H, 9.28; N, 4.70%.
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0034712156
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Wolfe J.P., Tomori H., Sadighi J.P., Yin J.J., Buchwald S.L. J. Org. Chem. 65:2000;1158-1174.
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