Multi-step reaction with 13 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 48 h / 10 - 35 °C
2.1: triethylamine / methanol / 72 h / 10 - 35 °C
3.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 2 h / 35 °C / Cooling with ice
3.2: 0.5 h
4.1: 1H-imidazole / tetrahydrofuran / 2 h / 35 °C / Cooling with ice
5.1: triethylamine / tetrahydrofuran / 1.5 h / 0 °C
6.1: sodium t-butanolate / tetrahydrofuran / 2 h / 35 °C / Cooling with ice
7.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere
7.2: 2 h / -78 - 35 °C
8.1: carbonochloridic acid 1-chloro-ethyl ester / acetonitrile / 0.25 h / 10 - 35 °C
8.2: 18 h / 80 °C
8.3: 2 h / 35 °C / Cooling with ice
9.1: CHIRALPAK AD / hexane; ethanol / Resolution of racemate
10.1: triethylamine / tetrahydrofuran / 2 h / Cooling with ice
11.1: N,N-dimethyl-formamide / 80 °C
12.1: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide / 1.5 h / 10 - 35 °C
13.1: sodium hydroxide; water / butan-1-ol / 4.5 h / 120 °C
With
1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; aluminum (III) chloride; sodium tetrahydroborate; lithium aluminium tetrahydride; carbonochloridic acid 1-chloro-ethyl ester; water; dihydrogen peroxide; potassium carbonate; triethylamine; calcium chloride; sodium hydroxide; sodium t-butanolate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;