acetic acid; acetyl chloride in ethanol 18 h; Heating / reflux;

sodium hypophosphite; 2-methyl propanoic acid; palladium on activated charcoal in 1,4-dioxane; water 8 h; Heating;

sodium hydroxide

1: 95 percent / NaOAc, NH2OH*HCl / ethanol; H2O / 1.) reflux, 5 h, 2.) room temperature, overnoght 2: 80 percent / HCl, H2 / 5percent Pd/C / ethanol / 4 h / 2068.6 Torr / Ambient temperature 3: 90 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 94 percent / 18 h / Ambient temperature 5: 98 percent / 5percent K2CO3 / methanol / 2 h / Heating 6: 64 percent / BF3*Et2O / CH2Cl2 / 16 h 7: 97 percent / 1N HCl / methanol / 24 h / 25 °C 8: 66 percent / H2O, paraformaldehyde / tetrahydrofuran / 2 h / Heating 9: TiCl4 / CH2Cl2; diethyl ether / 0.5 h / -78 °C 10: 10percent aq. NaOH / ethanol / 2 h / Heating View Scheme

4 A molecular sieve; potassium tert-butylate in tetrahydrofuran; tert-butyl alcohol T=20°C;

4 A molecular sieve; potassium tert-butylate in tetrahydrofuran

1: 11 h / Heating 2: LiAlH4 / tetrahydrofuran / 7 h / Heating 3: 1.) t.BuOK, 2.) aqueous AcOH (50percent) / 1.) DMSO, 90-110 deg C, 2 weeks, 2.) 95 deg C, 4 h View Scheme

methanol; hydrazine hydrate

1: 62 percent / NaH, tris<2-(2-methoxyethoxy)ethyl>amine / CH2Cl2 / 24 h / Ambient temperature 2: 78 percent / NaH2PO2*H2O / Pd/C (10percent) / H2O; dioxane / 8 h / Heating 3: 58 percent / aq. NaOH / methanol / 24 h / Ambient temperature View Scheme