dicyclohexyl-carbodiimide in tetrahydrofuran 24 h; Ambient temperature;

boron trifluoride diethyl etherate

F3B-OEt2; Mechanism;

1: 60.4 percent / dimethyl sulfoxide, HCl / 0.25 h / Ambient temperature 2: 74.5 percent / HCl (gas) / 1 h / Ambient temperature 3: 64.9 percent / phosphorus pentasulfide / pyridine / 3 h / Heating View Scheme

1: hydrogenchloride / 2.5 h / 110 °C 2: N-bromosuccinmide / dichloromethane / 2 h / 0 °C / |Inert atmosphere 3: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0.5 h / 20 °C 4: tetrakis(triphenylphosphine) palladium(0); isopropylamine; copper(l) iodide / ethylene glycol dimethyl ether / 3.5 h / 70 °C / |Inert atmosphere 5: hydrogen; palladium 10 on activated carbon / ethyl acetate / 0.75 h / |Inert atmosphere 6: diisobutylaluminium hydride / tetrahydrofuran / 0.25 h / 0 °C 7: dimethyl sulfoxide; sulfur trioxide pyridine complex; triethylamine / dichloromethane / 2 h / 0 °C 8: sodium acetate; hydroxylamine hydrochloride / isopropyl alcohol / 1.5 h / 20 °C 9: Acid orange 52; sodium cyanoborohydride; hydrogenchloride / methanol / 1 h / 20 °C 10: sodium cyanoborohydride / tert-butyl alcohol / 16 h / |Inert atmosphere; |Sealed tube; |Microwave irradiation 11: zinc; trifluoroacetic acid; water / dichloromethane / 20 °C View Scheme

1: With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethyl-formamide T=20°C; 2 h; 2: With hydroxylamine hydrochloride in N,N-dimethyl-formamide

silver tetrafluoroborate; palladium diacetate; trifluoroacetic acid in N,N-dimethyl-formamide T=90°C; 0.333333 h; Inert atmosphereMicrowave irradiationSealed tube;

bromine; mercury(II) oxide in tetrachloromethane; acetone T=55°C;

in benzene 1 h; Heating;

hydrogenchloride