ammonia in methanol T=20°C;

sodium tetrahydroborate in N,N-dimethyl-formamide T=20°C; 2 h;

1: triethylamine; acetonitrile / 1 h / Ambient temperature; other reagent 2: POCl3 / acetonitrile / 0.25 h / 0 °C 3: acetonitrile / 3 h / 0 °C 4: 1.62 g / acetic acid; methanol / 5 h / Ambient temperature 5: 97 percent / ethanol / 1.5 h / Ambient temperature View Scheme

1: P2S5 View Scheme

in ethanol 1.5 h; Ambient temperature;

1: 64 percent / dimethyldioxirane / CH2Cl2; acetone / 25 °C 2: 90 percent / 2N methanol. NH3 / CH2Cl2 / 25 °C View Scheme

1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min View Scheme

1: triethylamine / CH2Cl2 / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min View Scheme

1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min View Scheme

1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H2O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min View Scheme