1: With lithium aluminium tetrahydride in diethyl ether T=0 - 20°C; 3 h; Inert atmosphere; 2: With water; sodium hydroxide in diethyl ether T=20°C; 0.25 h; Inert atmosphere;

1: aq. NaOH / ethanol / 2 h / Heating 2: 72 percent / SOCl2 / 4 h / Heating 3: 86 percent / aq. NH3 / tetrahydrofuran / 4 h 4: 50 percent / LiAlH4 / tetrahydrofuran / 6 h / Heating 5: 88 percent / pyridine / 0 °C 6: Br2 / CH2Cl2 / 2 h 7: KOH / ethanol / 20 h / Heating 8: 50 percent / Et3N / CH2Cl2 / 24 h / Ambient temperature 9: 1.) O3, 2.) Me2S / 1) CH2Cl2, MeOH, -78 deg C; 2) CH2Cl2, MeOH, 4 h 10: 80 percent / immobilized penicillin acylase / ethanol / 0.5 h / 23 °C / pH 7.5 View Scheme

oxygen; copper dichloride; palladium dichloride in ethylene glycol dimethyl ether; water T=80°C; 6 h;

1: trimethylaluminum / toluene / 20 °C / Inert atmosphere 2: diethyl ether / 20 °C / Inert atmosphere 3: sodium tetrahydroborate / methanol / Inert atmosphere View Scheme

1: trimethylaluminum / toluene / 20 °C / Inert atmosphere 2: diethyl ether / 20 °C / Inert atmosphere View Scheme