N-(3-Benzyloxy-4-nitrobenzyl)-N-methylbenzenesulfonamide → N-(4-Amino-3-benzyloxybenzyl)-N-methylbenzenesulfonamide

Participants

Reaction Steps

To a suspension of N-(3-Benzyloxy-4-nitrobenzyl)-N-methylbenzenesulfonamide (1.09 g, 2.643 mmol) in EtOAc is added platinum oxide (60 mg). The reaction is placed under an atmosphere of H2 and stirred at RT for 50 min. Additional platinum oxide is added (60 mg) and the reaction is stirred under an atmosphere of H2 at RT for an additional 50 min. During this time, the reaction changes from a greenish brown slurry to a black slurry. The slurry is filtered through Celite to remove the catalyst and the filter cake is washed with several portions of EtOAc. The filtrate and washings are combined, and concentrated under vacuum to afford an orange oil. LC/MS shows a 1:1 mixture of starting material and product. The orange oil is re-dissolved in. EtOAc, slurried with platinum oxide (150 mg) and stirred under an atmosphere of H2 at room temperature for 1.5 h. The reaction mixture is filtered through Celite and the filter cake is washed with EtOAc. The filtrate is concentrated to afford the title compound: (M+1)+=383.

Provenance & Evidence