triethylamine in methanol

1: CH2Cl2 / 2 h / 23 °C 2: 96 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h 3: 1.) 1-(chlorocarbonyl)-1-methylene acetate, 2.) NaOMe / 1.) CHCl3, 23 deg C, 3 h, 2.) THF, 23 deg C, 4 h 4: 75 percent / propan-2-ol / 2 h / Heating View Scheme

1: CH2Cl2 / 2 h / 23 °C 2: 96 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h 3: 1.) 1-(chlorocarbonyl)-1-methylene acetate, 2.) NaOMe / 1.) CHCl3, 23 deg C, 3 h, 2.) THF, 23 deg C, 4 h 4: 75 percent / propan-2-ol / 2 h / Heating View Scheme

1: KOH / aq. ethanol / 3 h / 70 °C 2: CH2Cl2 / 2 h / 23 °C 3: 96 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h 4: 1.) 1-(chlorocarbonyl)-1-methylene acetate, 2.) NaOMe / 1.) CHCl3, 23 deg C, 3 h, 2.) THF, 23 deg C, 4 h 5: 75 percent / propan-2-ol / 2 h / Heating View Scheme

1: 96 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h 2: 1.) 1-(chlorocarbonyl)-1-methylene acetate, 2.) NaOMe / 1.) CHCl3, 23 deg C, 3 h, 2.) THF, 23 deg C, 4 h 3: 75 percent / propan-2-ol / 2 h / Heating View Scheme

1: 1-ethyl-3-<(3-dimethylamino)propyl>carbodiimide*HCl, 1-hydroxybenzotriazole hydrate, triethylamine / dimethylformamide / 18 h / Ambient temperature 2: trifluoroacetic acid / CHCl3 / 3 h / Ambient temperature 3: 47 percent / W-200-N alumina / tetrahydrofuran; diethyl ether / 72 h / Ambient temperature View Scheme

1: trifluoroacetic acid / CHCl3 / 3 h / Ambient temperature 2: 47 percent / W-200-N alumina / tetrahydrofuran; diethyl ether / 72 h / Ambient temperature View Scheme

1: 1.) 1-(chlorocarbonyl)-1-methylene acetate, 2.) NaOMe / 1.) CHCl3, 23 deg C, 3 h, 2.) THF, 23 deg C, 4 h 2: 75 percent / propan-2-ol / 2 h / Heating View Scheme

1: 1.) carbonyldiimidazole 2: NaBH4 / ethanol / 1 h / -15 - -10 °C 3: 80 percent / TsOH*H2O / 1.) r.t., 24 h, 2.) 50 deg C, 7 h 4: 100 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 5: (COCl)2, DMF / toluene / 1 h 6: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 7: aq. AcOH, conc. HCl / 3 h / Ambient temperature 8: 100 percent / KOH / methanol / 3 h / Ambient temperature 9: 84 percent / propan-2-ol / 1.) 70 deg C, 9 h, 2.) r.t., 16 h View Scheme

1: 2.) Bu4NF / 1.) THF 2: 19 percent / pyridine, 4-(dimethylamino)pyridine / 16 h / Ambient temperature 3: 13 percent / 1 M NaOH / ethanol / 0.25 h / Ambient temperature 4: 96 percent / acetonitrile / 20 h / Heating 5: NaBH4 / methanol / 1 h / -10 °C 6: HgCl2 / acetonitrile; H2O / 0.25 h 7: NaCNBH3, 1 M HCl, 3-Angstroem molecular sieves / methanol / 112 h / Ambient temperature View Scheme