hydrogen; palladium on activated charcoal in tetrahydrofuran; ethanol P=760 Torr; Ambient temperature;

1: 35.9 percent / Et3N / tetrahydrofuran / 1.) r.t., 2.) 60-70 deg C 2: 53.9 percent / hydrogen / 10 percent Pd-C / ethanol; tetrahydrofuran / 760 Torr / Ambient temperature View Scheme

1: 94.1 percent / pyridinium bromide perbromide, 30 percent HBr-AcOH / acetic acid / 1 h / Ambient temperature 2: 35.9 percent / Et3N / tetrahydrofuran / 1.) r.t., 2.) 60-70 deg C 3: 53.9 percent / hydrogen / 10 percent Pd-C / ethanol; tetrahydrofuran / 760 Torr / Ambient temperature View Scheme

1: 35.9 percent / Et3N / tetrahydrofuran / 1.) r.t., 2.) 60-70 deg C 2: 53.9 percent / hydrogen / 10 percent Pd-C / ethanol; tetrahydrofuran / 760 Torr / Ambient temperature View Scheme