1: LiBr 2: pyridine 3: NaN3 / dimethylformamide / Ambient temperature 4: HCl 5: H2S / pyridine View Scheme

1.) - 75 deg C, 2.) 25 deg C, 15 min; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

N,N,N',N',N'',N''-hexamethylphosphoric triamide in tetrahydrofuran; hexane T=-65°C;

1: LiBr 2: pyridine 3: NaN3 / dimethylformamide / Ambient temperature 4: HCl View Scheme

lithium bromide

1: 1.) n-BuLi / 1.) n-hexane - THF, -30 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 2: 80 percent / pyridinium tosylate / H2O / acetone / 4 h / Heating 3: 1.) n-BuLi / 1.) n-hexane - THF, -70 deg C, 20 min, 2.) 17 h, temperature gradually warmed to room temperature 4: 95 percent / hydrogen / 5percent Pd/C / ethanol / 20 h View Scheme