Multi-step reaction with 10 steps
1.1: sodium citrate / water / 0.2 °C / pH Ca545 / Enzymatic reaction
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 15 - 20 °C
2.2: 48 h / 1.8 - 20 °C
3.1: dichloromethane; acetic acid / 0.17 h / 20 °C
3.2: 1.17 h / 0 °C
4.1: potassium hydroxide / methanol / 4 h / 20 °C
4.2: pH 7
5.1: dimethyl sulfoxide; oxalyl dichloride; triethylamine / dichloromethane / 2.5 h / -70 °C / Inert atmosphere
6.1: (1R,2S)-2-(morpholin-4-yl)-1-phenyl-1-propanol; n-butyllithium / toluene; hexane / 1 h / 0 - 12 °C
6.2: 0 h / -10 - -5 °C
7.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 50 °C
7.2: 0 °C / pH 3
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C
9.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 15 h / 45 °C / Inert atmosphere
10.1: potassium hexamethylsilazane / tetrahydrofuran; 2-methyltetrahydrofuran / 2 h / -44 - 20 °C / Inert atmosphere
With
dmap; (1R,2S)-2-(morpholin-4-yl)-1-phenyl-1-propanol; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; water; sodium citrate; potassium hexamethylsilazane; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium hydroxide;
In
tetrahydrofuran; 2-methyltetrahydrofuran; methanol; hexane; dichloromethane; water; acetic acid; toluene;