Multi-step reaction with 11 steps
1.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 2 h / 35 °C / Cooling with ice
1.2: 0.5 h
2.1: 1H-imidazole / tetrahydrofuran / 2 h / 35 °C / Cooling with ice
3.1: triethylamine / tetrahydrofuran / 1.5 h / 0 °C
4.1: sodium t-butanolate / tetrahydrofuran / 2 h / 35 °C / Cooling with ice
5.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere
5.2: 2 h / -78 - 35 °C
6.1: carbonochloridic acid 1-chloro-ethyl ester / acetonitrile / 0.25 h / 10 - 35 °C
6.2: 18 h / 80 °C
6.3: 2 h / 35 °C / Cooling with ice
7.1: CHIRALPAK AD / hexane; ethanol / Resolution of racemate
8.1: triethylamine / tetrahydrofuran / 2 h / Cooling with ice
9.1: sodium azide / N,N-dimethyl-formamide / 70 °C
10.1: triphenylphosphine; water / tetrahydrofuran / 10 - 35 °C
11.1: acetonitrile / 12 h / 10 - 35 °C
With
1H-imidazole; aluminum (III) chloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; carbonochloridic acid 1-chloro-ethyl ester; water; triethylamine; triphenylphosphine; calcium chloride; sodium t-butanolate;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetonitrile;
10.1: Staudinger Reaction;