Multi-step reaction with 9 steps
1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride / 1.) RT, 2.) 25 deg C, 1 h
2: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 1.5 h / Heating
3: hydrogenchloride; potassium permanganate / 1.) H2O, 1 h, 2.) overnight
4: hydrogenchloride; hydrogen / platinum(IV) oxide / methanol / 6 h / 2585.7 Torr
5: triethylamine / tetrachloromethane / 3 h / 0 - 20 °C
6: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / Ambient temperature
7: triethylamine / tetrahydrofuran / 0.08 h
8: triethylamine / tetrahydrofuran; ethanol; water / 1 h / 55 °C
9: hydrogen bromide / acetic acid / 1.5 h / 130 °C
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); hydrogen bromide; hydrogen; sodium hydride; triethylamine;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; water; acetic acid;
DOI:10.1021/jm00147a046