Multi-step reaction with 7 steps
1.1: tetra-N-butylammonium tribromide / tetrahydrofuran; methanol / 20 °C
2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / 4 h / -20 °C / Inert atmosphere
2.2: 0.33 h / -20 - 20 °C
2.3: 18 h / 20 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 0.08 h / 0 °C
3.2: 0 - 20 °C
4.1: sodium iodide; sodium azide / N,N-dimethyl-formamide; water / 40 h / 80 °C
5.1: palladium 10% on activated carbon / methanol / 1 h / 80 °C
6.1: hydrogenchloride / 1,4-dioxane; methanol / 16 h / 20 °C
7.1: triethylamine / methanol / 1 h / 20 °C
7.2: 72 h / 20 °C
With
2,6-dimethylpyridine; hydrogenchloride; sodium azide; dimethylsulfide borane complex; tetra-N-butylammonium tribromide; triethylamine; sodium iodide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;