1: 92 percent / NaN3 / dimethylsulfoxide / 12 h / 25 °C 2: 97 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / 0 °C 3: 81 percent / LiBH4 / tetrahydrofuran / 3 h / 0 °C 4: 90 percent / nBu4NF / tetrahydrofuran / 1 h / 25 °C 5: HS(CH2)3SH, Et3N / methanol / 24 h / 25 °C View Scheme

1: 92 percent / NaN3 / dimethylsulfoxide / 12 h / 25 °C 2: 97 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / 0 °C 3: 81 percent / LiBH4 / tetrahydrofuran / 3 h / 0 °C 4: 90 percent / nBu4NF / tetrahydrofuran / 1 h / 25 °C View Scheme