1: 1.) LDA / 1.) THF, hexane, -80 deg C, 1 h, 2.) THF, hexane, -60 deg C, 2 h 2: 83 percent / pyridine / Ambient temperature 3: 10 percent / LiAlH4 / tetrahydrofuran / 1 h / 25 °C / other tosylates; var. temperatures, solvents and reaction time View Scheme

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sodium hydroxide in methanol 12 h; Heating; Yield given;

potassium hydroxide

graphite oxide in chloroform-d1 T=200°C; 12 h; Molecular sieve;

1.1: C2H5ONa / ethanol / 1 h / Heating 1.2: 61 percent / ethanol / 4 h / Heating 2.1: 70 percent / H2; aq. HCl / Pd/C / methanol / 72 h / 36775.4 Torr 3.1: BH3*THF / tetrahydrofuran / 8 h / Heating View Scheme

sodium amide; methyl iodide