hydrogen; palladium on activated charcoal in methanol

potassium hydroxide; hydrazine hydrate in diethylene glycol 7 h; Heating;

1: 88 percent / NaBH4 / 3 h / Ambient temperature 2: 1.) 10percent KOH / 1.) MeOH, H2O, reflux, 30 min; 2.) 180 deg C, 4 h 3: 59 percent / LiAlH4 / tetrahydrofuran / 6 h / Heating 4: 20 percent / hexamethylphosphoric acid triamide / 0.5 h / Heating 5: 80 percent / H2 / 5percent Pd-C / methanol View Scheme

1: 1.) 10percent KOH / 1.) MeOH, H2O, reflux, 30 min; 2.) 180 deg C, 4 h 2: 59 percent / LiAlH4 / tetrahydrofuran / 6 h / Heating 3: 20 percent / hexamethylphosphoric acid triamide / 0.5 h / Heating 4: 80 percent / H2 / 5percent Pd-C / methanol View Scheme

1: 20 percent / hexamethylphosphoric acid triamide / 0.5 h / Heating 2: 80 percent / H2 / 5percent Pd-C / methanol View Scheme

1: 59 percent / LiAlH4 / tetrahydrofuran / 6 h / Heating 2: 20 percent / hexamethylphosphoric acid triamide / 0.5 h / Heating 3: 80 percent / H2 / 5percent Pd-C / methanol View Scheme

1: KO-t-Bu / 2-methyl-propan-2-ol; dimethylsulfoxide 2: 60 percent / KOH, hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 7 h / Heating View Scheme

1: KO-t-Bu / 2-methyl-propan-2-ol; dimethylsulfoxide 2: 60 percent / KOH, hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 7 h / Heating View Scheme