sodium hydride

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 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 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 View Scheme

1.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 2 h / 20 °C / Inert atmosphere 1.2: 3 h / Inert atmosphere 2.1: tetrahydrofuran; methanol / 2.5 h / 20 °C / Inert atmosphere; Molecular sieve 3.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere 4.1: boron tribromide / dichloromethane / 16 h / 0 °C / Reflux; Inert atmosphere View Scheme

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;