1: HCl, H2O / 24 h / 45 °C 2: H2O / 18 h / 110 °C 3: SOCl2 / 16 h / -60 - 20 °C 4: 97 percent / HCl, H2O / 24 h / 40 °C 5: 58 percent / H2 / 20percent Pd(OH)2/C / ethanol / 16 h / 759.8 Torr / Ambient temperature View Scheme

1: 1.) NaH, 2.) NaOH 2: 75 percent / aq. sodium chloride / dimethylformamide / 3 h / Heating 3: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h 4: 53 percent / H2 / 10percent Pd/C / methanol / 2250.2 Torr View Scheme

1: 1.) NaH, 2.) NaOH 2: 75 percent / Na(Hg), disodium hydrogen phosphate / methanol; tetrahydrofuran 3: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h 4: 53 percent / H2 / 10percent Pd/C / methanol / 2250.2 Torr View Scheme

1: 75 percent / aq. sodium chloride / dimethylformamide / 3 h / Heating 2: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h 3: 53 percent / H2 / 10percent Pd/C / methanol / 2250.2 Torr View Scheme

1: 84 percent / 1,1,3,3-tetramethylquanidine / 24 h / 20 °C 2: 82 percent / Porcine liver acetone powder; sodium hydroxide; phosphate buffer / 2 h / 20 °C / pH 7 3: hydrogen; Raney nickel / ethanol / 3 h / 20 °C / 760 Torr 4: 0.60 g / toluene; ethanol / Heating 5: 100 percent / trimethylchlorosilane / 20 °C 6: 90 percent / 4-dimethylaminopyridine; triethylamine / CH2Cl2 / 1 h / 20 °C 7: BH3-DMS / tetrahydrofuran / -10 - 20 °C 8: 0.16 g / hydrochloric acid / ethanol; tetrahydrofuran / 1 h / Heating 9: 100 percent / Amberlite IRA 400 (OH(1-)); aqueous acetic acid View Scheme

1: 90 percent / 4-dimethylaminopyridine; triethylamine / CH2Cl2 / 1 h / 20 °C 2: BH3-DMS / tetrahydrofuran / -10 - 20 °C 3: 0.16 g / hydrochloric acid / ethanol; tetrahydrofuran / 1 h / Heating 4: 100 percent / Amberlite IRA 400 (OH(1-)); aqueous acetic acid View Scheme

1: 100 percent / trimethylchlorosilane / 20 °C 2: 90 percent / 4-dimethylaminopyridine; triethylamine / CH2Cl2 / 1 h / 20 °C 3: BH3-DMS / tetrahydrofuran / -10 - 20 °C 4: 0.16 g / hydrochloric acid / ethanol; tetrahydrofuran / 1 h / Heating 5: 100 percent / Amberlite IRA 400 (OH(1-)); aqueous acetic acid View Scheme