1.1: 6 N aq. HCl / 6 h / Heating 2.1: POCl3 / 4 h / Heating 3.1: 7.80 g / -40 - 20 °C 4.1: 49 percent / diethyl ether / 2 h / -40 °C 5.1: Na2CO3; 1-chloroethyl chloroformate / 1,2-dichloro-ethane / 3 h / Heating 5.2: 86 percent / MeOH / 20 °C View Scheme

1: 0.75 N aq. HCl / 3 h / Heating 2: POCl3 / Heating 3: 168 h / Ambient temperature 4: 2.) trifluoroacetic acid / 1.) Et2O, -40 deg C, 3 h, 2.) Et2O, -78 deg C, 1 h 5: 1.25 h / 120 °C 6: AcOH, Zn / 24 h / Ambient temperature View Scheme

1: 86 percent / conc. HCl / 24 h / Heating 2: 93 percent / H2 / Pd/C / methanol / 6.5 h / 3102.9 Torr / Ambient temperature 3: 1.) (COCl)2, DMF, 2.) N-hydroxy-2-thiopyridone / 1.) CH2ClCH2Cl, room temperature, 12 h, 2.) CH2ClCH2Cl, room temperature, 1.5 h, 3.) CH2Cl2, irradiation, 0 deg C, 2 h 4: toluene / 24 h / Heating 5: 2.) Et3N / 1.) MeOH, reflux, 2 h, 2.) MeOH, room temperature, 15 h 6: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 7: 78 percent / Na2CO3*H2O / tetrahydrofuran; H2O / 16 h 8: 96 percent / aq. NaOH / ethanol / 1.) 0 deg C, 1 h, 2.) room temperature, 1.5 h 9: 80 percent / 0.67 h / 105 - 110 °C 10: 94 percent / Na2CO3, aq. H2O2 / H2O / 24 h / Ambient temperature 11: 96 percent / DMAP / CH2Cl2 / 12 h / Ambient temperature 12: 90 percent / TFA / CH2Cl2 / 1 h / Ambient temperature 13: 75 percent / NaBH3CN / acetonitrile / 1 h / Ambient temperature 14: 93 percent / NaNO2 / acetic acid; acetic anhydride / 1.) 0 deg C, 16 h, 2.) room temperature, 8 h 15: 95 percent / CH2Cl2 View Scheme

NADP T=25°C; pH=7.8; 0.166667 h; Enzyme kinetics; Further Variations:Solvents;

ammonia; water

hydrogenchloride 22 h; Heating;

1.1: vinyl chloroformate / 1,2-dichloro-ethane / 12 h / Heating 1.2: 82 percent / HCl / methanol / 16 h / Heating 2.1: 89 percent / NaHCO3 / benzene / 6 h / 20 °C View Scheme

1.1: hydrogenchloride; water / |Heating 2.1: trichlorophosphate 3.1: hydrogenchloride 4.1: diethyl ether / -45 °C 4.2: -78 °C 5.1: 2 h / 120 °C 6.1: acetic acid; zinc / 16 h / 20 °C 7.1: triethylamine / acetonitrile / 5 h / 80 °C / |Inert atmosphere 8.1: pyridine / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere; |Cooling with ice 9.1: hydrogenchloride / methanol / 80 °C 10.1: 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane; potassium fluoride / acetonitrile / 0.08 h / 110 °C / |Sealed tube View Scheme

1.1: hydrogenchloride; water / |Heating 2.1: trichlorophosphate 3.1: hydrogenchloride 4.1: diethyl ether / -45 °C 4.2: -78 °C 5.1: 2 h / 120 °C 6.1: acetic acid; zinc / 16 h / 20 °C 7.1: sodium carbonate / acetonitrile / 2 h / 130 °C View Scheme

hydrogenchloride 24 h; Heating;