1: 94 percent / dimethylformamide / 15 h / 20 °C 2: hydrobromic acid; acetic acid 3: potassium carbonate 4: borane-tetrahydrofuran complex / acetonitrile / 3 h / 20 °C 5: 85 percent / toluene / 20 h / Heating 6: 88 percent / borane-tetrahydrofuran complex / tetrahydrofuran / 3 h / 20 °C 7: 90 percent / hydrogen / Pd/C / methanol / 2 h / 20 °C / 760 Torr View Scheme

1: aqueous ethanol 2: aqueous HCl View Scheme

1: 78 percent / K2CO3, KI / acetone / 168 h / Ambient temperature 2: H2, acetic acid / 10percent Pd/C / methanol / 16 h / 2280 Torr 3: K2CO3 / acetone / 16 h / Ambient temperature 4: 1) KH, 2) HCl / 1) THF/hexane, 0 deg C, 2) MeOH, reflux, 2 h View Scheme

1: 95 percent / K2CO3, KI / acetone / 3 h 2: HCl / methanol / 1 h / Heating 3: NaCNBH3 / methanol / 1 h / Heating 4: K2CO3, KI / acetone / 16 h 5: 1) LDA, 2) HCl / 1) THF/hexane, -50 deg C, 30 min, 2) reflux, 4 h View Scheme

in methanol Yield given;

hydrogenchloride