Multi-step reaction with 18 steps
1.1: 42.55 g / imidazole / dimethylformamide / 24 h
2.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C
2.2: hexane; tetrahydrofuran / 1 h / -78 °C
3.1: 8.35 g / aq. HF / acetonitrile / 20 °C
4.1: H2 / Pd/C / dioxane / 12 h / 20 °C / 760 Torr
4.2: 83 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
5.1: pyridine / CH2Cl2 / 0 °C
6.1: aq. K2CO3 / methanol / 5 h
7.1: Dess-Martin reagent / CH2Cl2 / 3 h / 0 °C
8.1: CF3SO3H; Et3B; DIPEA / hexane; CH2Cl2 / 0.5 h / -10 °C
8.2: 91 percent / TiCl4 / hexane; CH2Cl2 / 2 h
9.1: LiAlH4 / tetrahydrofuran / 0.5 h / Heating
10.1: PPTs / 24 h
11.1: 82 percent / 2,4,6-trichlorobenzoyl chloride; DIPEA; DMAP / benzene
12.1: TsOH / methanol
13.1: 2,2,6,6-tetramethylpiperidinyloxyl; KBr; NaHCO3 / NaClO / CH2Cl2; H2O / 1 h
14.1: NaClO2; NaH2PO4 / H2O; 2-methyl-propan-2-ol; various solvent(s) / 1 h
15.1: HATU; DIPEA / CH2Cl2 / 24 h
16.1: 86 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 3 h / -78 °C
17.1: N-methylaniline / [Pd(PPh3)4] / tetrahydrofuran / 2 h
18.1: HATU; DIPEA / CH2Cl2 / 48 h / 20 °C
With
pyridine; 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl; triethyl borane; trifluorormethanesulfonic acid; diethylamino-sulfur trifluoride; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; lithium diisopropyl amide;
sodium hypochlorite; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
2.2: Peterson reaction / 7.1: Dess-Martin oxidation;
DOI:10.1002/chem.200600599