hydrogen; palladium on activated charcoal in ethyl acetate 4 h;

hydrogen; palladium on activated charcoal in methanol; water P=362.004 Torr; 1.5 h; Ambient temperaturepH 7 phosphate buffer; Yield given. Title compound not separated from byproducts;

1: 100 percent / NaH / tetrahydrofuran / 2 h / 0 °C 2: 100 percent / H2 / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature 3: Et3N / CH2Cl2 / 1 h 4: CH2Cl2 / 1 h 5: 86 percent / anisole, TiCl4 / CH2Cl2 / 1 h / 0 °C 6: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C 7: 98 percent / Et3N / toluene / 5 h / Ambient temperature 8: 1.) NaH, 2.) benzyl bromide / 1.) THF, toluene, -20 deg C, 1 h, 2.) THF, toluene, -20 deg C, 2 h 9: DBU / toluene; tetrahydrofuran / 2 h 10: 89 percent / phosphate buffer pH 3 / 2.5 h / Ambient temperature View Scheme