hydrogenchloride in ethanol

tetrabutyl ammonium fluoride in tetrahydrofuran 2 h; 0 to 25 deg C;

hydrogenchloride; Dowex 1-X8 a) MeOH, reflux, 30 min, b) H2O;

ammonium hydroxide 12 h;

1: 0.09 g / sodium bicarbonate / methanol; H2O / 3 h / 0 °C 2: trifluoroacetic acid / H2O / 2.5 h / 25 °C 3: 0.032 g / H2 / Pd/C / methanol / 12 h / 4137.18 Torr View Scheme

1.1: In / tetrahydrofuran / Heating 1.2: (+)-cinchonine / tetrahydrofuran / 20 °C 1.3: 87 percent / tetrahydrofuran / 2 h / -78 °C 2.1: 98 percent / imidazole / dimethylformamide / 6 h / 20 °C 3.1: O3 / methanol / -78 °C 3.2: Me2S / methanol / 12 h / -78 - 20 °C 4.1: 1.01 g / H2 / Pd(OH)2/C / ethanol / 10 h / 20 °C 5.1: 90 percent / aq. K2CO3 / CH2Cl2 / 0.5 h / 20 °C 6.1: 93 percent / Dowex 50W-X8 / aq. methanol / 18 h / 20 °C 7.1: 99 percent / imidazole / CH2Cl2 / 1 h / 20 °C 8.1: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 9.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 11.1: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1: 92 percent / imidazole / dimethylformamide; CH2Cl2 / -60 °C 2: DBU / acetonitrile / 0 °C 3: 1.) methyl 2,2,2-trichloroacetimidate, Et3N, 2.) PPTS / 1.) MeCN, -20 to -15 deg C, 2.) MeOH, H2O, 20 deg C 4: 84 percent / H2O2 / H2O; tetrahydrofuran / 0 - 20 °C 5: 92 percent / Bu4NF / tetrahydrofuran / -5 - 0 °C 6: 88 percent / DIAD, PPh3 / tetrahydrofuran / 0 °C 7: 90 percent / tetrahydrofuran / 20 °C 8: Et3N / CH2Cl2 / Heating 9: TsOH / methanol / 20 °C 10: imidazole / dimethylformamide; CH2Cl2 / -60 °C 11: 91 percent / OsO4, NMO, H2O / acetone / 0 °C 12: 92 percent / TsOH / 20 °C 13: DMAP, Et3N / CH2Cl2 / 20 °C 14: Bu4NF / tetrahydrofuran / 20 °C 15: NaOH, H2O 16: 76 percent / cyclohexene / 5percent Pd/C / ethanol / Heating 17: 96 percent / HCl, H2O / methanol View Scheme

1: 90 percent / tetrahydrofuran / 20 °C 2: Et3N / CH2Cl2 / Heating 3: TsOH / methanol / 20 °C 4: imidazole / dimethylformamide; CH2Cl2 / -60 °C 5: 91 percent / OsO4, NMO, H2O / acetone / 0 °C 6: 92 percent / TsOH / 20 °C 7: DMAP, Et3N / CH2Cl2 / 20 °C 8: Bu4NF / tetrahydrofuran / 20 °C 9: NaOH, H2O 10: 76 percent / cyclohexene / 5percent Pd/C / ethanol / Heating 11: 96 percent / HCl, H2O / methanol View Scheme

1: 88 percent / DIAD, PPh3 / tetrahydrofuran / 0 °C 2: 90 percent / tetrahydrofuran / 20 °C 3: Et3N / CH2Cl2 / Heating 4: TsOH / methanol / 20 °C 5: imidazole / dimethylformamide; CH2Cl2 / -60 °C 6: 91 percent / OsO4, NMO, H2O / acetone / 0 °C 7: 92 percent / TsOH / 20 °C 8: DMAP, Et3N / CH2Cl2 / 20 °C 9: Bu4NF / tetrahydrofuran / 20 °C 10: NaOH, H2O 11: 76 percent / cyclohexene / 5percent Pd/C / ethanol / Heating 12: 96 percent / HCl, H2O / methanol View Scheme

1: Et3N / CH2Cl2 / Heating 2: TsOH / methanol / 20 °C 3: imidazole / dimethylformamide; CH2Cl2 / -60 °C 4: 91 percent / OsO4, NMO, H2O / acetone / 0 °C 5: 92 percent / TsOH / 20 °C 6: DMAP, Et3N / CH2Cl2 / 20 °C 7: Bu4NF / tetrahydrofuran / 20 °C 8: NaOH, H2O 9: 76 percent / cyclohexene / 5percent Pd/C / ethanol / Heating 10: 96 percent / HCl, H2O / methanol View Scheme