trifluoroacetic acid in dichloromethane

sodium carbonate in methanol 12 h;

1.1: 80 percent / sodium borohydride / methanol / 0 - 20 °C 2.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 3.1: 90 percent / potassium carbonate / methanol 4.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 4.2: tetrahydrofuran / -78 °C 5.1: TFA / CH2Cl2 / 10 h View Scheme

1.1: nBuLi / hexane; tetrahydrofuran / 0.33 h / 0 °C 1.2: 80 percent / hexane; tetrahydrofuran / 2 h / 20 °C 2.1: 98 percent / H2 / Pd/C / methanol / 8 h / 20 °C 3.1: 97 percent / aq. HCl / methanol / 1 h / 20 °C 4.1: 75 percent / pyridine / 12 h / -17 °C 5.1: 89 percent / ethanol; H2O / 12 h / 20 °C 6.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasonic irradiation 6.2: 69 percent / tetrahydrofuran / 5.5 h / 50 °C / ultrasonic irradiation 7.1: 84 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 98 percent / H2 / Pd/C / methanol / 8 h / 20 °C 2.1: 97 percent / aq. HCl / methanol / 1 h / 20 °C 3.1: 75 percent / pyridine / 12 h / -17 °C 4.1: 89 percent / ethanol; H2O / 12 h / 20 °C 5.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasonic irradiation 5.2: 69 percent / tetrahydrofuran / 5.5 h / 50 °C / ultrasonic irradiation 6.1: 84 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 2.1: 90 percent / potassium carbonate / methanol 3.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 3.2: tetrahydrofuran / -78 °C 4.1: TFA / CH2Cl2 / 10 h View Scheme

1.1: 85 percent / NaH; n-BuLi / tetrahydrofuran / 0 °C 2.1: 80 percent / sodium borohydride / methanol / 0 - 20 °C 3.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h 4.1: 90 percent / potassium carbonate / methanol 5.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 5.2: tetrahydrofuran / -78 °C 6.1: TFA / CH2Cl2 / 10 h View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran / -78 °C 2.1: TFA / CH2Cl2 / 10 h View Scheme

1.1: 75 percent / pyridine / 12 h / -17 °C 2.1: 89 percent / ethanol; H2O / 12 h / 20 °C 3.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasonic irradiation 3.2: 69 percent / tetrahydrofuran / 5.5 h / 50 °C / ultrasonic irradiation 4.1: 84 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: Zn / tetrahydrofuran / 0.17 h / 50 °C / ultrasonic irradiation 1.2: 69 percent / tetrahydrofuran / 5.5 h / 50 °C / ultrasonic irradiation 2.1: 84 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 20 °C View Scheme