Multi-step reaction with 9 steps
1.1: sodium azide / N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere
2.1: trimethylphosphane / tetrahydrofuran; water / 1 h / 25 °C / Inert atmosphere
3.1: sodium hydrogencarbonate / methanol; water / Inert atmosphere; Reflux
4.1: Chiralcel OD-H / hexane; isopropyl alcohol / Resolution of racemate
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C / Inert atmosphere
5.2: 5 h / 0 - 25 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere
7.1: sodium periodate; ruthenium(III) trichloride hydrate / tetrachloromethane; water; acetonitrile / 3 h / 25 °C / Inert atmosphere
8.1: thionyl chloride / 0 - 25 °C / Inert atmosphere
9.1: ammonia / methanol / 120 h / 25 °C / Inert atmosphere; Sealed tube
9.2: 72 h / 50 °C / Inert atmosphere; Sealed tube
With
sodium periodate; thionyl chloride; sodium azide; ruthenium(III) trichloride hydrate; ammonia; sodium hydride; sodium hydrogencarbonate; lithium hexamethyldisilazane; trimethylphosphane;
In
tetrahydrofuran; methanol; tetrachloromethane; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; mineral oil;
DOI:10.1021/jm300354j