Multi-step reaction with 11 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: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.33 h
11.1: hydrogen / platinum on activated charcoal / methanol / 1 h / Inert atmosphere
With
1H-imidazole; aluminum (III) chloride; sodium tetrahydroborate; lithium aluminium tetrahydride; carbonochloridic acid 1-chloro-ethyl ester; hydrogen; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; calcium chloride; sodium t-butanolate;
platinum on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; acetonitrile;