1: 63 percent / (Me3Si)2NNa 2: 60 percent / H(1+) View Scheme

1: 1.) BuLi / 1.) ether, 2 h 2: H2 / 5percent Pd/C / ethyl acetate / 20 °C View Scheme

1: 63 percent / (Me3Si)2NNa 2: 60 percent / H(1+) 3: 85 percent / LiAlH4 View Scheme

1: 1) sodium silazide (NaHMDS) / 1) Et2O, r.t., 2) -78 deg C to r.t., 12 h 2: 73 percent / dimethylsulfoxide / 20 h / Ambient temperature 3: 1) BuLi / 1) hexane, THF, -30 deg C, 2) THF, -50 deg C to r.t., 2 h View Scheme

1: 1.) BuLi / 1.) ether, 2 h 2: H2 / 5percent Pd/C / ethyl acetate / 20 °C 3: LiAlH4 / diethyl ether / 2 h / 4 °C 4: 8 h / 100 °C View Scheme

1: 1) sodium silazide (NaHMDS) / 1) Et2O, r.t., 2) -78 deg C to r.t., 12 h 2: 73 percent / dimethylsulfoxide / 20 h / Ambient temperature 3: 1) BuLi / 1) hexane, THF, -30 deg C, 2) THF, -50 deg C to r.t., 2 h 6: 83 percent / Py / tetrahydrofuran / 1) -20 deg C, 0.5 h, 2) r.t., 3 h View Scheme

1: 1) sodium silazide (NaHMDS) / 1) Et2O, r.t., 2) -78 deg C to r.t., 12 h 2: 73 percent / dimethylsulfoxide / 20 h / Ambient temperature 3: 1) BuLi / 1) hexane, THF, -30 deg C, 2) THF, -50 deg C to r.t., 2 h 6: 68 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme