Multi-step reaction with 11 steps
1.1: sodium hydrogencarbonate; sodium hypochlorite; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 0 °C
2.1: formic acid / water; methanol / 24 h / 40 °C
3.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere
3.2: 0.33 h / -78 °C
3.3: -40 °C
4.1: Chiralpak Daicel.(R). AD-20 / isopropyl alcohol / Resolution of racemate
5.1: hydrogen / tetrahydrofuran / 3 h / 25 °C
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 1.5 h / -78 °C
7.1: sodium hydroxide / water; methanol / 3 h / 20 °C
7.2: pH 2 - 3
8.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
9.1: triethylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
10.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 0.83 h / 100 °C / Inert atmosphere
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 50 °C
With
1H-imidazole; sodium hypochlorite; n-butyllithium; formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; sodium carbonate; triethylamine; diisopropylamine; HATU; sodium bromide; sodium hydroxide; lithium hexamethyldisilazane;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;