1: With 9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran T=20°C; 12 h; 2: With hydroxylamine-o-sulphonic acid in tetrahydrofuran T=70°C; 3 h; Title compound not separated from byproducts;

1: 1) H2SO4, AcOH; / 1) 60 deg C, 1 day; 2) Amberlite IR-120(H+), 70 deg C, 15 h 2: 60 percent / NaH / dimethylformamide 4: 73 percent / LDA, MoOPH / tetrahydrofuran / -78 - 20 °C 5: 69 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature 6: 83 percent / NaIO4 / H2O; acetone / 0.25 h / Ambient temperature 7: 76 percent / PDC / dimethylformamide / 19 h / Ambient temperature 8: 67 percent / iodobenzenediacetate, I2 / CCl4 / 0.25 h / Heating; Irradiation 9: 99 percent / N-Bu3SnH / diethyl ether / 10 h / Heating 10: 74 percent / p-TsOH / methanol / 0.67 h / Ambient temperature 11: 71 percent / (PhO)2P(O)N3,Ph3P, (NCO2Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature 12: 43 percent / n-Bu3SnH / benzene / 1.5 h / Heating View Scheme

1: 60 percent / NaH / dimethylformamide 3: 73 percent / LDA, MoOPH / tetrahydrofuran / -78 - 20 °C 4: 69 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature 5: 83 percent / NaIO4 / H2O; acetone / 0.25 h / Ambient temperature 6: 76 percent / PDC / dimethylformamide / 19 h / Ambient temperature 7: 67 percent / iodobenzenediacetate, I2 / CCl4 / 0.25 h / Heating; Irradiation 8: 99 percent / N-Bu3SnH / diethyl ether / 10 h / Heating 9: 74 percent / p-TsOH / methanol / 0.67 h / Ambient temperature 10: 71 percent / (PhO)2P(O)N3,Ph3P, (NCO2Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature 11: 43 percent / n-Bu3SnH / benzene / 1.5 h / Heating View Scheme

1.1: NaH / tetrahydrofuran / 1 h / 0 °C 1.2: tetrahydrofuran / 2 h / -40 °C 2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 3.1: NaH / tetrahydrofuran / 1 h / 20 °C 3.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C 4.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C 4.2: hydroxylamine-O-sulfonic acid / tetrahydrofuran / 3 h / 70 °C View Scheme

1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C 3.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C 3.2: hydroxylamine-O-sulfonic acid / tetrahydrofuran / 3 h / 70 °C View Scheme

1.1: NaH / tetrahydrofuran / 1 h / 0 °C 1.2: tetrahydrofuran / 2 h / -40 °C 2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 3.1: NaH / tetrahydrofuran / 1 h / 20 °C 3.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C 4.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C 4.2: hydroxylamine-O-sulfonic acid / tetrahydrofuran / 3 h / 70 °C View Scheme

1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C 2.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C 2.2: hydroxylamine-O-sulfonic acid / tetrahydrofuran / 3 h / 70 °C View Scheme

1: 71 percent / (PhO)2P(O)N3,Ph3P, (NCO2Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature 2: 43 percent / n-Bu3SnH / benzene / 1.5 h / Heating View Scheme

1: 80 percent / p-TsOH / benzene / Ambient temperature 2: 86 percent / (PHO)2P(O)N3, Ph3P, (NCO2Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature 3: 89 percent / 80percent aq. AcOH / 7 h / Ambient temperature 4: 92 percent / NaIO4 / dioxane; H2O / 0.17 h / Ambient temperature 5: 93 percent / H2CrO4 / acetone / 10 h / 0 °C 6: 54 percent / iodobenzenediacetate, I2 / CCl4 / 0.25 h / Heating; Irradiation 7: 19 percent / n-Bu3SnH / benzene / 1.5 h / Heating View Scheme

1: 99 percent / N-Bu3SnH / diethyl ether / 10 h / Heating 2: 74 percent / p-TsOH / methanol / 0.67 h / Ambient temperature 3: 71 percent / (PhO)2P(O)N3,Ph3P, (NCO2Et)2 / tetrahydrofuran / 0.17 h / Ambient temperature 4: 43 percent / n-Bu3SnH / benzene / 1.5 h / Heating View Scheme