triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran 1.5 h; 0 deg C to RT;

1: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 2: 100 percent / acetonitrile / 48 h / Heating 3: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 4: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 5: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 6: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 7: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 8: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

1: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C 2: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 3: 100 percent / acetonitrile / 48 h / Heating 4: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 5: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 6: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 7: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 8: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 9: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

1: 100 percent / acetonitrile / 48 h / Heating 2: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 3: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 4: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 5: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 6: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 7: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

1: p-TsOH / H2O; tetrahydrofuran / 0.17 h / Heating 2: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C 3: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 4: 100 percent / acetonitrile / 48 h / Heating 5: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 6: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 7: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 8: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 9: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 10: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

1: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 2: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 3: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 4: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 5: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 6: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

1: 100 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 2: p-TsOH / H2O; tetrahydrofuran / 0.17 h / Heating 3: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C 4: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 5: 100 percent / acetonitrile / 48 h / Heating 6: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 7: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 8: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 9: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 10: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 11: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

1: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 2: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 3: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 4: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

1: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 2: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 3: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 4: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 5: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

carbon palladium in ethanol