Multi-step reaction with 14 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 - -40 °C / Inert atmosphere
1.2: 2.25 h / -78 - 20 °C
2.1: L-proline / dimethyl sulfoxide / 8 h / 50 °C
3.1: pyridine; trichlorophosphate / 0 - 20 °C
4.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.5 h / -23 °C
4.2: 0.75 h
5.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere
5.2: 12 h / 40 °C
6.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
6.2: 2 h / 0 - 20 °C
7.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: hydrogenchloride; methanol / dichloromethane / 20 °C
9.1: pyridine / dmap / dichloromethane / 0.75 h / 0 °C / Inert atmosphere
10.1: diethylamino-sulfur trifluoride / dichloromethane / 16 h / 20 °C / Inert atmosphere
11.1: sodium methylate; methanol / 20 °C / Industry scale
12.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere
12.2: 2 h / 20 °C
13.1: dibromo sulfoxide / dichloromethane / 5 h / -40 - 0 °C / Inert atmosphere
13.2: 1 h / 0 °C
14.1: tri-n-butyl-tin hydride / toluene / 110 °C
With
pyridine; 1H-imidazole; hydrogenchloride; methanol; dibromo sulfoxide; oxalyl dichloride; diethylamino-sulfur trifluoride; cerium(III) chloride heptahydrate; dimethylsulfide borane complex; tri-n-butyl-tin hydride; sodium methylate; Dess-Martin periodane; dimethyl sulfoxide; L-proline; trichlorophosphate;
dmap;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;