triethylamine in dichloromethane T=20°C; 12 h;

hydrogen; {(1,5-cyclooctadiene)Rh(1,2-bis((2S,5S)-2,5-diethylphospholano)benzene)}triflate in tetrahydrofuran T=20 - 25°C; Catalytic hydrogenation; P=1551.44 Torr; 12 h; Title compound not separated from byproducts;

1: base 2: LiAlH4 / tetrahydrofuran 3: H2 / (S,S)-[(Et-DuPHOS)Rh(COD)]OTf / tetrahydrofuran / 12 h / 20 - 25 °C / 1551.44 Torr View Scheme

1: 9.15 g / diisopropylethylamine / CH2Cl2 / 2 h 2: 13.61 g / imidazole / dimethylformamide / 6 h 3: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 4: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 5: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 6: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: 13.61 g / imidazole / dimethylformamide / 6 h 2: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 3: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 4: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 5: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 2: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 3: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 4: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 2: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 3: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 2: Bu4NF / tetrahydrofuran / 1 h / 4 °C View Scheme

jones reagent in acetone 0.333333 h; Yield given;

methanol; Amberlyst 15; ammonia 1.) CH2Cl2, 25 deg C, 6 h, 2.) 50 min; Yield given. Multistep reaction;