hydrogen; palladium on activated charcoal in acetic acid; isopropyl alcohol T=50°C; P=4500.36 Torr; 15 h;

sodium hydroxide; water in isopropyl alcohol T=79°C; 5.33333 h; Heating / reflux;

lithium aluminium tetrahydride in diethyl ether T=0 - 20°C;

trifluoroacetic acid in dichloromethane T=20°C; Boc-deprotection; 0.25 h;

1: With potassium hydroxide in toluene 2 h; Heating / reflux; 2: With water in toluene T=90 - 95°C; 0.5 h;

1.1: NaH / dimethylformamide / 0.33 h / 20 °C 1.2: 52 percent / dimethylformamide / 14 h / 90 °C 2.1: 96 percent / hydrogen / Pd/C / acetic acid; propan-2-ol / 15 h / 50 °C / 4500.36 Torr View Scheme

1.1: 100 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: NaH / dimethylformamide / 0.33 h / 20 °C 2.2: 52 percent / dimethylformamide / 14 h / 90 °C 3.1: 96 percent / hydrogen / Pd/C / acetic acid; propan-2-ol / 15 h / 50 °C / 4500.36 Torr View Scheme

1: 77 percent / Et3N / tetrahydrofuran / 4 h / Heating 2: Na2CO3 / CH2Cl2 / 0.5 h 3: 8.36 g / EtONa / ethanol / 0.5 h / Heating 4: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 5: 79 percent / MeOH; NaH / toluene / 4 h / Heating 6: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 7: CAN / acetonitrile; H2O / 0.5 h / 20 °C 8: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 9: Cs2CO3 / o-xylene / 20 h / 130 °C 10: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

1: Na2CO3 / CH2Cl2 / 0.5 h 2: 8.36 g / EtONa / ethanol / 0.5 h / Heating 3: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 4: 79 percent / MeOH; NaH / toluene / 4 h / Heating 5: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 6: CAN / acetonitrile; H2O / 0.5 h / 20 °C 7: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 8: Cs2CO3 / o-xylene / 20 h / 130 °C 9: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

1: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 2: 79 percent / MeOH; NaH / toluene / 4 h / Heating 3: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 4: CAN / acetonitrile; H2O / 0.5 h / 20 °C 5: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 6: Cs2CO3 / o-xylene / 20 h / 130 °C 7: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme