Multi-step reaction with 12 steps
1.1: 4-methylmorpholine / tetrahydrofuran / 20 h / -10 °C
2.1: NaBH4 / H2O / 5 h / 23 °C
3.1: 7.6 g / imidazole / dimethylformamide
4.1: H2 / Pd/C / ethanol / 23 °C / 2585.81 Torr
5.1: 4.85 g / i-Pr2NEt; HATU / dimethylformamide / 1.42 h / 0 - 23 °C
6.1: i-Pr2NEt / CH2Cl2
7.1: NaH / tetrahydrofuran / 0.33 h
7.2: 77 percent / NaH / tetrahydrofuran / 61 h / Heating
8.1: aq. triethylamine trihydrofluoride / acetonitrile / 23 °C
9.1: Dess-Martin periodinane / CH2Cl2 / 2 h
10.1: 0.710 g / tetrahydrofuran / 1 h / Heating
11.1: 1.08 h / 190 - 200 °C
12.1: 4-methylmorpholine / acetonitrile / 0 - 23 °C
With
4-methyl-morpholine; 1H-imidazole; sodium tetrahydroborate; triethylamine trihydrofluoride; hydrogen; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
10.1: Wittig olefination;
DOI:10.1021/jm010469k