hydrogenchloride

[(S)-BINAPRuCl(benzene)]Cl; hydrogen in methanol T=20 - 50°C; P=3750.38 Torr; 12 h; AutoclaveInert atmosphere; Overall yield = 89.2 percent; enantioselective reaction;

1: aq. NaOH 2: aq. NaOH View Scheme

sodium hydroxide

1: water; acetone / 6 h / |Reflux 2: [(S)-BINAPRuCl(benzene)]Cl; hydrogen / methanol / 12 h / 20 - 50 °C / 3750.38 Torr / |Autoclave; |Inert atmosphere View Scheme

1: sodium acetate; acetic anhydride / 3.75 h / 40 - 135 °C 2: water; acetone / 6 h / |Reflux 3: [(S)-BINAPRuCl(benzene)]Cl; hydrogen / methanol / 12 h / 20 - 50 °C / 3750.38 Torr / |Autoclave; |Inert atmosphere View Scheme

1: sulfuryl chloride 3: 87.5 mg / 1-hydroxybenzotriazole; triethylamine; 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran; CH2Cl2 / 0 - 20 °C 4: hydrogen / Pd(OH)2 on carbon / ethyl acetate / 2 h / 20 °C 5: 89 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH2Cl2 / 18 h / 20 °C 6: CH2Cl2 / 0 - 20 °C 7: 31.0 mg / NaHCO3; diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C 8: 55 percent / dimethyldioxirane / CH2Cl2; acetone / -30 - 20 °C View Scheme