Multi-step reaction with 14 steps
1.1: triethylamine / methanol / 72 h / 10 - 35 °C
2.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 2 h / 35 °C / Cooling with ice
2.2: 0.5 h
3.1: 1H-imidazole / tetrahydrofuran / 2 h / 35 °C / Cooling with ice
4.1: triethylamine / tetrahydrofuran / 1.5 h / 0 °C
5.1: sodium t-butanolate / tetrahydrofuran / 2 h / 35 °C / Cooling with ice
6.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere
6.2: 2 h / -78 - 35 °C
7.1: carbonochloridic acid 1-chloro-ethyl ester / acetonitrile / 0.25 h / 10 - 35 °C
7.2: 18 h / 80 °C
7.3: 2 h / 35 °C / Cooling with ice
8.1: CHIRALPAK AD / hexane; ethanol / Resolution of racemate
9.1: Dess-Martin periodane / acetonitrile / 3 h / Cooling with ice
10.1: 2-methyl-but-2-ene; potassium dihydrogenphosphate; sodium chlorite / water; tert-butyl alcohol; tetrahydrofuran / 2 h / Cooling with ice
11.1: triethylamine; diphenyl phosphoryl azide / toluene / 0.5 h / 90 °C
11.2: 2 h / 90 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 50 °C
13.1: acetonitrile / 10 - 35 °C
14.1: hydrogenchloride / ethyl acetate / 2 h / 10 - 35 °C
With
1H-imidazole; hydrogenchloride; aluminum (III) chloride; sodium chlorite; sodium tetrahydroborate; potassium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; carbonochloridic acid 1-chloro-ethyl ester; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; calcium chloride; sodium t-butanolate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol;
11.1: Curtius Rearrangement;