Multi-step reaction with 12 steps
1.1: NaHDMS / tetrahydrofuran / 2 h / -78 °C
1.2: 80 percent / tetrahydrofuran / -78 - -20 °C
2.1: 92 percent / LiOH*H2O; aq. H2O2 / tetrahydrofuran / 2 h / 20 °C
3.1: 96 percent / H2; K2CO3 / Pd/C / methanol / 0.83 h
4.1: EDC; DMAP / dimethylformamide / 12 h / 50 °C
5.1: ((S)-1-Ph-2-piperidin-1-yl-Et)-(2,2,2-triF-Et)amine; n-BuLi / tetrahydrofuran; hexane / 1 h
5.2: Me3SiCl / 0.58 h / -78 - 0 °C
6.1: 0.310 g / LiAlH4 / tetrahydrofuran / 5 h / Heating
7.1: n-Bu2SnO / toluene / 0.75 h / Heating
7.2: 71 percent / CH2Cl2 / 1 h / 0 °C
8.1: imidazole / dimethylformamide / 3 h / 65 °C
8.2: dimethylformamide / 20 h / 80 °C
9.1: 0.174 g / DDQ / CH2Cl2; H2O / 1.5 h / 20 °C
10.1: O3; N-methylmorpholine N-oxide; benzyl ethyl eter / CH2Cl2 / 0.13 h / -78 °C
10.2: 80 percent / NaBH4 / methanol / 1 h / -40 - -10 °C
11.1: DMSO; (COCl)2; Et3N / CH2Cl2 / 1.67 h / -78 - 0 °C
12.1: 0.112 g / Bn2NH*CF3COOH / toluene / 16 h / 45 °C
With
1H-imidazole; dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; di(n-butyl)tin oxide; potassium carbonate; ozone; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
5.1: Ireland-Claisen rearrngement / 11.1: Swern oxidation reaction;
DOI:10.1016/j.tetlet.2007.07.182