in diethyl ether T=0°C; 12 h;

1: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 2: LiAlH4 / tetrahydrofuran / 50 - 60 °C 3: HBr / 120 - 130 °C 4: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 5: PCl5 / 6 h / Ambient temperature 6: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: SOCl2, DMF 2: Heating 3: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 4: LiAlH4 / tetrahydrofuran / 50 - 60 °C 5: HBr / 120 - 130 °C 6: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 7: PCl5 / 6 h / Ambient temperature 8: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: Heating 2: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 3: LiAlH4 / tetrahydrofuran / 50 - 60 °C 4: HBr / 120 - 130 °C 5: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 6: PCl5 / 6 h / Ambient temperature 7: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: piperidine / pyridine / 110 - 130 °C 2: SOCl2, DMF 3: Heating 4: H2 / Pd/C / tetrahydrofuran / 40 - 50 °C 5: LiAlH4 / tetrahydrofuran / 50 - 60 °C 6: HBr / 120 - 130 °C 7: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 8: PCl5 / 6 h / Ambient temperature 9: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: HBr / 120 - 130 °C 2: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 3: PCl5 / 6 h / Ambient temperature 4: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 2: PCl5 / 6 h / Ambient temperature 3: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: LiAlH4 / tetrahydrofuran / 50 - 60 °C 2: HBr / 120 - 130 °C 3: 1) lithium diisopropylamide / 1) hexane, THF, 50 deg C, 2.5 h, 2) THF, a) r.t., 2 h, b) 40 deg C, 1 h 4: PCl5 / 6 h / Ambient temperature 5: 75 percent / diethyl ether / 12 h / 0 °C View Scheme

1: PCl5 / 6 h / Ambient temperature 2: 75 percent / diethyl ether / 12 h / 0 °C View Scheme