1.1: lithium tri-t-butoxyaluminum hydride / ethanol / 2 h / -78 °C / Inert atmosphere 2.1: Grubb's 2nd generation catalyst / dichloromethane / 24 h / Inert atmosphere; Reflux 3.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 25 °C 4.1: pyridine / dichloromethane / 4 h / 25 °C / Inert atmosphere 5.1: toluene-4-sulfonic acid / methanol / 2 h / 25 °C / Inert atmosphere 5.2: 2 h / 25 °C / Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 48 h / 90 °C / Inert atmosphere 7.1: palladium 10 on activated carbon; hydrogen / methanol / 3 h / 25 °C View Scheme

1.1: lithium tri-t-butoxyaluminum hydride / ethanol / 2 h / -78 °C / Inert atmosphere 2.1: Grubb's 2nd generation catalyst / dichloromethane / 24 h / Inert atmosphere; Reflux 3.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 25 °C 4.1: pyridine / dichloromethane / 4 h / 25 °C / Inert atmosphere 5.1: toluene-4-sulfonic acid / methanol / 2 h / 25 °C / Inert atmosphere 5.2: 2 h / 25 °C / Inert atmosphere View Scheme