Multi-step reaction with 10 steps
1.1: 1H-imidazole / 4 h / 150 °C
2.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran; toluene / 4 h / 80 °C
3.1: sodium tetrahydroborate / methanol / 0.75 h / 0 - 20 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1.75 h / 0 - 20 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 - -40 °C
5.2: 15.25 h / -78 - 20 °C
6.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.5 h / 20 °C
7.1: methanol; lithium hydroxide; water / 12 h / 20 °C
7.2: pH ~ 2
8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
10.1: ammonium acetate; sodium cyanoborohydride / methanol / 2 h / Heating / reflux
With
1H-imidazole; methanol; lithium hydroxide; sodium tetrahydroborate; tributylphosphine; ammonium acetate; water; iodine; potassium hexamethylsilazane; sodium cyanoborohydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; 1,1'-azodicarbonyl-dipiperidine;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;