LS-Selectridereg; in tetrahydrofuran T=-78°C; 0.166667 h;

trifluoroacetic acid

1: DCC / CH2Cl2 / Ambient temperature 2: imidazole / dimethylformamide / 1.5 h / 5 °C 3: N2O4, NaOAc / CCl4 / 0.25 h / 5 °C 4: LiBH4 / tetrahydrofuran / Ambient temperature 5: 83 g / pyridine / 2.5 h / Ambient temperature 6: 46.4 g / 0.5 N H2SO4 / acetonitrile / 17 h / Ambient temperature 7: 90 percent / LS-Selectride / tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: 92 percent / 2 N KOH / methanol / 1 h / 43 °C 2: DCC / CH2Cl2 / Ambient temperature 3: imidazole / dimethylformamide / 1.5 h / 5 °C 4: N2O4, NaOAc / CCl4 / 0.25 h / 5 °C 5: LiBH4 / tetrahydrofuran / Ambient temperature 6: 83 g / pyridine / 2.5 h / Ambient temperature 7: 46.4 g / 0.5 N H2SO4 / acetonitrile / 17 h / Ambient temperature 8: 90 percent / LS-Selectride / tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: N2O4, NaOAc / CCl4 / 0.25 h / 5 °C 2: LiBH4 / tetrahydrofuran / Ambient temperature 3: 83 g / pyridine / 2.5 h / Ambient temperature 4: 46.4 g / 0.5 N H2SO4 / acetonitrile / 17 h / Ambient temperature 5: 90 percent / LS-Selectride / tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: LiBH4 / tetrahydrofuran / Ambient temperature 2: 83 g / pyridine / 2.5 h / Ambient temperature 3: 46.4 g / 0.5 N H2SO4 / acetonitrile / 17 h / Ambient temperature 4: 90 percent / LS-Selectride / tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: 83 g / pyridine / 2.5 h / Ambient temperature 2: 46.4 g / 0.5 N H2SO4 / acetonitrile / 17 h / Ambient temperature 3: 90 percent / LS-Selectride / tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: 46.4 g / 0.5 N H2SO4 / acetonitrile / 17 h / Ambient temperature 2: 90 percent / LS-Selectride / tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: imidazole / dimethylformamide / 1.5 h / 5 °C 2: N2O4, NaOAc / CCl4 / 0.25 h / 5 °C 3: LiBH4 / tetrahydrofuran / Ambient temperature 4: 83 g / pyridine / 2.5 h / Ambient temperature 5: 46.4 g / 0.5 N H2SO4 / acetonitrile / 17 h / Ambient temperature 6: 90 percent / LS-Selectride / tetrahydrofuran / 0.17 h / -78 °C View Scheme

1: 84 percent / 8 h / 57 °C 2: 51 percent / K2CO3, 18-crown-6 / dimethylformamide / 21 h / 110 °C 3: 1.) NaOMe, 2.) 3N HCl / 1.) MeOH, 40 deg C, 2 h, 2.) 50 deg C, 2 h View Scheme