Multi-step reaction with 9 steps
1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
1.2: 2.25 h / -40 °C
2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux
3.1: hydrogen / palladium 10% on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr
4.1: hydrogenchloride; 2-amino-2-hydroxymethyl-1,3-propanediol; water; HLAP / 48 h / 40 °C / Enzymatic reaction
4.2: 20 °C / pH 3.5
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere
5.2: 20 °C
6.1: potassium carbonate; tetrabutyl-ammonium chloride; sodium hydrogencarbonate / N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 3 h / 20 °C
7.1: pyridine; titanium tetrachloride / dichloromethane; tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere
8.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 24 h / 760.05 Torr
9.1: triethylamine / dmap / 3 h / Inert atmosphere
With
pyridine; hydrogenchloride; lithium aluminium tetrahydride; HLAP; tetrabutyl-ammonium chloride; water; hydrogen; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 2-amino-2-hydroxymethyl-1,3-propanediol; lithium diisopropyl amide;
dmap; N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; camphor-10-sulfonic acid;
In
tetrahydrofuran; methanol; n-heptane; dichloromethane; water; toluene; benzene;
7.1: Knoevenagel Condensation;