1: LiAlH4 2: p-tosyl chloride View Scheme

1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 °C 3: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / dichloromethane / 4 h / 20 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: K₂CO₃ / dimethylformamide<br />2: 49 g<br />3: K₂CO₃ / dimethylformamide<br />4: H₂ / 10percent Pd-C / ethyl acetate / 8 h / 80 &deg;C / 38000 Torr<br />5: 8 g<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: sulfuric acid / 24 h / Reflux<br />2: lithium / methanol / 48 h / Reflux<br />3: sulfuric acid / 24 h / Reflux<br />4: palladium 10 on activated carbon; hydrogen / methanol / 24 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: lithium / methanol / 48 h / Reflux<br />2: sulfuric acid / 24 h / Reflux<br />3: palladium 10 on activated carbon; hydrogen / methanol / 24 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: sulfuric acid / 24 h / Reflux<br />2: palladium 10 on activated carbon; hydrogen / methanol / 24 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 49 g<br />2: K₂CO₃ / dimethylformamide<br />3: H₂ / 10percent Pd-C / ethyl acetate / 8 h / 80 &deg;C / 38000 Torr<br />4: 8 g<br /> <br /> &nbsp;