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Initial attempts to construct the diazepanone via deprotection of the Cbz group in a model compound such as A followed by reductive amination of the aldehyde, both promoted by catalytic hydrogenation with Pd/C, were unsuccessful because of difficulty in hydrogenating the corresponding cyclic imine. Additional forcing conditions under medium pressure gave a 5,6-dihydrouridine derivative B due to over-reduction Chemical Equation Presented
-
Initial attempts to construct the diazepanone via deprotection of the Cbz group in a model compound such as A followed by reductive amination of the aldehyde, both promoted by catalytic hydrogenation with Pd/C, were unsuccessful because of difficulty in hydrogenating the corresponding cyclic imine. Additional forcing conditions under medium pressure gave a 5,6-dihydrouridine derivative B due to over-reduction (Chemical Equation Presented)
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