hydrogen; palladium on activated charcoal in ethyl acetate P=760 Torr; Ambient temperature;

1: Et3N / tetrahydrofuran / a) -78 deg C, 10 min, b) 0 deg C, 30 min 2: 1) n-BuLi / 1) hexane, THF, -78 deg C, 2) a) -78 deg C, 15 min, b) up to room temp., 45 min 3: 1) KHMDS, 2) trisyl azide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 min 4: aq. LiOH, 30percent H2O2 / tetrahydrofuran; H2O / 1 h / 0 °C 5: H2 / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature View Scheme

1: 1) n-BuLi / 1) hexane, THF, -78 deg C, 2) a) -78 deg C, 15 min, b) up to room temp., 45 min 2: 1) KHMDS, 2) trisyl azide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 min 3: aq. LiOH, 30percent H2O2 / tetrahydrofuran; H2O / 1 h / 0 °C 4: H2 / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature View Scheme

1: 1) KHMDS, 2) trisyl azide / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 min 2: aq. LiOH, 30percent H2O2 / tetrahydrofuran; H2O / 1 h / 0 °C 3: H2 / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature View Scheme

1: aq. LiOH, 30percent H2O2 / tetrahydrofuran; H2O / 1 h / 0 °C 2: H2 / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature View Scheme

water; lithium hydroxide hydrate in tetrahydrofuran; methanol T=0°C; 6 h;

1: Et3N / tetrahydrofuran 2: diethyl ether 3: aq. C6H5CO2Ag / dioxane / 20 °C / sonication View Scheme

Multistep reaction;

trifluoroacetic acid in dichloromethane 0.5 h;