hydrogen; platinum(IV) oxide in ethanol

1: triethylamine / dichloromethane 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 110 °C 3: water; sodium hydroxide / ethanol / 2 h / Reflux View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 110 °C 2: water; sodium hydroxide / ethanol / 2 h / Reflux View Scheme

1: sodium hydride / tetrahydrofuran 2: sodium tetrahydroborate / methanol / -78 °C 3: triethylamine / dichloromethane 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 110 °C 5: water; sodium hydroxide / ethanol / 2 h / Reflux View Scheme

(i) KNH2, liq. NH3, (ii) /BRN= 969135/; Multistep reaction;