1: HCl / methanol / 3 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 3: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 4: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 5: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 6: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 7: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 8: 3 N HCl / ethyl acetate / 1 h / 25 °C 9: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C 10: 57 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C View Scheme

1: HCl / methanol / 3 h / 25 °C 2: H2 / 10percent Pd/C / methanol / 6 h / 25 °C 3: EDCI, HOBt*H2O / dimethylformamide / 16 h / 25 °C 4: 1.) NaH, CuBr-SMe2 / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h 5: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C 6: 53 percent / EDCI, HOBt*H2O / dimethylformamide / 12 h / 25 °C 7: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C 8: 3 N HCl / ethyl acetate / 1 h / 25 °C 9: 58 percent / NaHCO3, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C View Scheme