triethylamine in dichloromethane T=20°C;

dicyclohexyl-carbodiimide in chloroform Ambient temperature;

1: CHCl3 / Ambient temperature 2: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 3: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating View Scheme

1: CHCl3 / Ambient temperature 2: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 3: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating 4: 62.6 percent / iodomonochloride / acetic acid / 3.5 h / Ambient temperature View Scheme

1: CHCl3 / Ambient temperature 2: 89 percent / borane-THF / tetrahydrofuran / 24 h / Ambient temperature 3: 88.9 percent / SnCl2, conc. HCl / aq. ethanol / 3 h / Heating 4: 62.6 percent / iodomonochloride / acetic acid / 3.5 h / Ambient temperature 5: 1.) NaNO2, HCl, 2.) NaN3 / 1.) water, 0-5 deg C, 1 h, 2.) 30 min View Scheme