1: aqueous NaOH 2: SOCl2 3: aqueous NaOH 4: platinum; ethanol / Hydrogenation View Scheme

1: lithium borohydride / tetrahydrofuran / 21 h / 25 °C / |Inert atmosphere 2: dipyridinium dichromate / dichloromethane / 11 h / 25 °C / |Inert atmosphere View Scheme

lithium borohydride in tetrahydrofuran T=25°C; 21 h; Inert atmosphere;

1: lithium borohydride / tetrahydrofuran / 21 h / 25 °C / |Inert atmosphere 2: dipyridinium dichromate / dichloromethane / 11 h / 25 °C / |Inert atmosphere 3: sodium dithionite; water / tetrahydrofuran / 1 h / 60 °C 4: N-benzyl-trimethylammonium hydroxide / tetrahydrofuran / 1 h / 0 °C 5: hydrogen; palladium 10 on activated carbon; formic acid / 3 h / 760.05 Torr View Scheme