Multi-step reaction with 15 steps
1.1: HCl / ethyl acetate / 1 h
2.1: 72 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH2Cl2 / 15 h / 4 °C
3.1: 100 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
4.1: HCl / dioxane / 0.5 h
5.1: 60 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19 h / 0 - 20 °C
6.1: LiOH / tetrahydrofuran; H2O / 2 h / 0 - 20 °C
7.1: 77 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 15 h / 0 - 20 °C
8.1: 75 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C
9.1: morpholine / (PPh3)4Pd / tetrahydrofuran / 2 h
10.1: HCl / dioxane / 1.5 h / 0 °C
11.1: 84 percent / pentafluorophenyl diphenylphosphinate; N,N-diisopropylethylamine / CH2Cl2 / 17 h / 20 °C
12.1: zinc; acetic acid / tetrahydrofuran / 4.5 h
12.2: 77 percent / triethylamine / tetrahydrofuran / 6 h / 0 - 20 °C
13.1: 100 percent / H2 / Pd(OH)2 / ethyl acetate / 3 h / 20 °C / 760 Torr
14.1: HCl / dioxane / 2.5 h / 0 - 20 °C
15.1: 211 mg / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 18 h / 0 - 20 °C
With
morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; diethyl cyanophosphonate; pentafluorophenyl diphenyl-phosphinate; tetrabutyl ammonium fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc;
palladium dihydroxide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.12.009