hydrogen; palladium on activated charcoal in methanol; ethyl acetate Ambient temperature;

1.1: imidazole / CH2Cl2 1.2: 25 percent / methanesulfonamide; t-butyl alcohol; AD mix α / H2O / 30 h 2.1: 85 percent / hydroxylamine hydrochloride; pyridine / ethanol / 72 h / 90 °C 3.1: 30 percent / DIAD; PPh3 / toluene / 1 h / Heating View Scheme

1: With triethylamine; trichlorophosphate in tetrahydrofuran T=-45 - -35°C; 3 - 5 h; 2: With water T=15 - 20°C; 24 - 26 h; Product distribution / selectivity;

1: With triethylamine; trichlorophosphate 2: With hydrogenchloride; water in ethyl acetate Product distribution / selectivity;

1: With 1H-tetrazole in tetrahydrofuran T=20°C; 0.333333 h; 2: With 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran; dichloromethane T=-70 - 20°C; 0.0833333 h;

1: With 1H-tetrazole in tetrahydrofuran T=20°C; 0.333333 h; 2: With 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran; dichloromethane T=-70 - 20°C; 0.0833333 h;

2: MCPBA View Scheme