1: 1) CH3I, 2) HCl / 1) 60 deg C, 5 h, 2) n-pentane, H2O, 25 deg C, 1 h 2: 95 percent / 4-DMAP, Et3N / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 3: 95 percent / H2 / Pd(OH)2-C / tetrahydrofuran / 0.25 h / 25 °C / 2585.7 Torr 4: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 45 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min View Scheme

1: 1) CH3I, 2) HCl / 1) 60 deg C, 5 h, 2) n-pentane, H2O, 25 deg C, 1 h 2: 98 percent / NaBH4 / methanol / 0.25 h / 0 °C View Scheme