1: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C -> room temp. 2: H2, 8percent NH3 / Raney Nickel / ethanol / 750.06 Torr 3: 61 percent / 36percent aq. HCl / 15 h / Heating View Scheme

1: H2, 8percent NH3 / Raney Nickel / ethanol / 750.06 Torr 2: 61 percent / 36percent aq. HCl / 15 h / Heating View Scheme

sodium azide; sulfuric acid in chloroform T=20°C;

1: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating; Irradiation 2: 0.75 h / 145 - 150 °C 3: hydrogen / Adams catalyst / methanol / 3 h / 3040 Torr 4: 3.1 g / 10 M hydrochloric acid / 10 h / Heating 5: 98percent sulfuric acid, sodium azide / CHCl3 / 20 °C View Scheme

1: 0.75 h / 145 - 150 °C 2: hydrogen / Adams catalyst / methanol / 3 h / 3040 Torr 3: 3.1 g / 10 M hydrochloric acid / 10 h / Heating 4: 98percent sulfuric acid, sodium azide / CHCl3 / 20 °C View Scheme