diisobutylaluminium hydride in diethyl ether; hexane T=-78°C; 0.5 h;

1.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C 2.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C 2.2: 74 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran; dioxane / 5 h / 85 °C 3.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C View Scheme

1.1: LiAlH4 / tetrahydrofuran / 16 h / 20 °C 2.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C 3.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C 3.2: 74 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran; dioxane / 5 h / 85 °C 4.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C View Scheme

1.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C 1.2: 74 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran; dioxane / 5 h / 85 °C 2.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C View Scheme

1: 1.) n-BuLi / 1.) THF 2: 2.) LiAlH4 / 1.) Et2O, -70 deg C, 2.) Et2O, 0 deg C, 3 h View Scheme

1: 1.) CBr4, Ph3P, 2.) (NH2CH2)2 / 1.) CH2Cl2, room temp., 1 h, 2.) DMSO, 8 deg C 2: 1.) n-BuLi / 1.) THF 3: 2.) LiAlH4 / 1.) Et2O, -70 deg C, 2.) Et2O, 0 deg C, 3 h View Scheme

2: 1.) CBr4, Ph3P, 2.) (NH2CH2)2 / 1.) CH2Cl2, room temp., 1 h, 2.) DMSO, 8 deg C 3: 1.) n-BuLi / 1.) THF 4: 2.) LiAlH4 / 1.) Et2O, -70 deg C, 2.) Et2O, 0 deg C, 3 h View Scheme

lithium aluminium tetrahydride 1.) Et2O, -70 deg C, 2.) Et2O, 0 deg C, 3 h; Yield given. Multistep reaction;