1: 89 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 2: 1.) CH3SO2Cl, Et3N, 2.) Bu4NN3 / 1.) CH2Cl2, -50 deg C, 1 h, 2.) THF, 9 h View Scheme

tetra-N-butylammonium azide; methanesulfonyl chloride; triethylamine 1.) CH2Cl2, -50 deg C, 1 h, 2.) THF, 9 h; Yield given. Multistep reaction;

1: 1) n-BuLi / 1) ether, hexane, -78 deg C, 5 min, 2) a) to 23 deg C, 2 h, b) 23 deg C, 8 h 2: 89 percent / imidazole / tetrahydrofuran / 8 h / 23 °C 3: 74 percent / LiClO4 / diethyl ether / 24 h / 23 °C 4: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 5: Et3N / CH2Cl2 / 1 h / -50 °C 6: Bu4NN3 / tetrahydrofuran / 2 h 7: Bu4NN3 / tetrahydrofuran / 9 h View Scheme

1: 1) n-BuLi / 1) ether, hexane, -78 deg C, 5 min, 2) a) to 23 deg C, 2 h, b) 23 deg C, 8 h 2: 89 percent / imidazole / tetrahydrofuran / 8 h / 23 °C 3: 74 percent / LiClO4 / diethyl ether / 24 h / 23 °C 4: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 5: Et3N / CH2Cl2 / 1 h / -50 °C 6: Bu4NN3 / tetrahydrofuran / 2 h 7: Bu4NN3 / tetrahydrofuran / 9 h View Scheme

1: 89 percent / imidazole / tetrahydrofuran / 8 h / 23 °C 2: 74 percent / LiClO4 / diethyl ether / 24 h / 23 °C 3: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 4: Et3N / CH2Cl2 / 1 h / -50 °C 5: Bu4NN3 / tetrahydrofuran / 2 h 6: Bu4NN3 / tetrahydrofuran / 9 h View Scheme

1: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 2: Et3N / CH2Cl2 / 1 h / -50 °C 3: Bu4NN3 / tetrahydrofuran / 2 h 4: Bu4NN3 / tetrahydrofuran / 9 h View Scheme

n-Bu4N3

2: LiClO4 3: LiAlH4 4: Et3N 5: n-Bu4N3 View Scheme

1: LiClO4 2: LiAlH4 3: Et3N 4: n-Bu4N3 View Scheme

1: LiAlH4 2: Et3N 3: n-Bu4N3 View Scheme