Now the amide carbonyl must be reduced with solutions

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Unformatted text preview: ? O ? H N CO2H CO2H Purpose of the problem Reduction, selectivity, and protection in two related sequences. Suggested solution The nitro group must be reduced to an amino group and cyclised onto the ketone or the carboxylic acid. Reductive amination (p. 234- 7 in the textbook) allows the amine to cyclise onto the more electrophilic ketone. NO2 O H2, Pd H N NH2 O CO2H HOAc CO2H H2, Pd H N CO2H CO2H these intermediates are not isolated— the cyclisation and reduction happen spontaneously Forming the six- membered ring requires more control. Protection of the ketone (say as the acetal) before reduction will give the six- membered cyclic amide. Now the...
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