lithium aluminium tetrahydride; (S)-2-(2,6-xylidinomethyl)pyrrolidine in diethyl ether T=-72°C; 6 h;

tert.-butyl lithium in tetrahydrofuran T=-78 - 0°C;

1: n-BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 0 deg C, 5 h 2: SeO2, 2-hydroxybenzoic acid, 80percent t-BuOOH / CH2Cl2 / 30 h / Ambient temperature 3: 79 percent / 1 M DIBAL / toluene / 0.5 h / -78 °C 4: 95 percent / BaMnO4 / CH2Cl2 / 8 h / Ambient temperature 5: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 6: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 7: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme

1: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 2: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 3: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme

1: 93 percent / PPh3, CCl4 / 1 h / Heating 2: 87 percent / 1 M DIBAL / hexane; toluene / 1 h / -78 °C 3: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 4: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 5: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme

1: 87 percent / 1 M DIBAL / hexane; toluene / 1 h / -78 °C 2: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 3: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 4: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme

1: 79 percent / 1 M DIBAL / toluene / 0.5 h / -78 °C 2: 95 percent / BaMnO4 / CH2Cl2 / 8 h / Ambient temperature 3: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 4: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 5: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme

1: SeO2, 2-hydroxybenzoic acid, 80percent t-BuOOH / CH2Cl2 / 30 h / Ambient temperature 2: 79 percent / 1 M DIBAL / toluene / 0.5 h / -78 °C 3: 95 percent / BaMnO4 / CH2Cl2 / 8 h / Ambient temperature 4: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 5: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 6: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme

1: 95 percent / BaMnO4 / CH2Cl2 / 8 h / Ambient temperature 2: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 3: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 4: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme

1: SeO2, 2-hydroxybenzoic acid, 80percent t-BuOOH / CH2Cl2 / 30 h / Ambient temperature 2: 93 percent / PPh3, CCl4 / 1 h / Heating 3: 87 percent / 1 M DIBAL / hexane; toluene / 1 h / -78 °C 4: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C 5: 15 percent / 1 M LiN(SiMe3)2 / tetrahydrofuran / 0.33 h / 55 °C 6: 72 percent / LiAlH4, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C View Scheme