Multi-step reaction with 14 steps
1.1: H2SO4
1.2: pyridine / ethanol
2.1: triethylamine / dimethylformamide
3.1: potassium carbonate / dimethylformamide
4.1: 42 g / H2 / Pd/C / ethanol
5.1: triethylamine
6.1: NaBH4 / methanol; tetrahydrofuran
7.1: triethylamine / dimethylformamide / 5 h / 20 °C
7.2: 6.46 g / DIBAL-H / tetrahydrofuran; toluene / 1 h / 0 °C
8.1: 61 percent / triphenylphosphine; DIAD / toluene; tetrahydrofuran / 3 h / 20 °C
9.1: TFA / CH2Cl2 / 1 h / 0 °C
10.1: 3.24 g / 1-hydroxy-7-azabenzotriazole; HATU; DIEA / dimethylformamide / 20 °C
11.1: 13 percent / Grubb's first generation catalyst / CH2Cl2 / 12 h / 40 °C
12.1: mercaptoacetic acid; LiOH*H2O / dimethylformamide / 1 h / 20 °C
13.1: 382 mg / HATU; triethylamine / dimethylformamide / 20 °C
14.1: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 96 h / -20 °C
With
lithium hydroxide; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; di-isopropyl azodicarboxylate; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; mercaptoacetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
palladium on activated charcoal; Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
8.1: Mitsunobu reaction;
DOI:10.1039/b702649h