Multi-step reaction with 12 steps
1.1: hydrogen bromide; acetic acid / dichloromethane / 3 h / 0 - 20 °C
2.1: tetra-(n-butyl)ammonium iodide; sodium tetrahydroborate / acetonitrile / 16 h / 40 °C / Molecular sieve
3.1: sodium methylate / methanol / 3 h / 50 °C
4.1: (1S)-10-camphorsulfonic acid / 2 h / 50 °C
5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C
5.2: 0.5 h
6.1: trifluoroacetic acid; water / dichloromethane / 0 °C
7.1: tetrabutyl-ammonium chloride; sodium hydrogencarbonate; sodium hypochlorite; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / ethyl acetate / 16 h / 20 °C
8.1: triethylamine; dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C
9.1: triethylsilyl trifluoromethyl sulfonate / dichloromethane / 2 h / -40 °C / Industry scale; Inert atmosphere
10.1: trifluoroacetic acid / 4 h / -5 - 20 °C / Industry scale
11.1: 1H-imidazole / dichloromethane / -20 - 20 °C / Inert atmosphere; Industry scale
12.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 10 - 20 °C / Inert atmosphere; Industry scale
With
1H-imidazole; dmap; sodium hypochlorite; sodium tetrahydroborate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (1S)-10-camphorsulfonic acid; tetrabutyl-ammonium chloride; water; hydrogen bromide; triethylsilyl trifluoromethyl sulfonate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium bromide;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile;