1: 82 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature 2: tetrahydrofuran / 48 h / 80 °C View Scheme

1: 99 percent / CH2Cl2 / 1 h / 0 °C 2: 82 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature 3: tetrahydrofuran / 48 h / 80 °C View Scheme

1: 1.) NaH / 1.) THF, 45 deg C, 4 h, 2.) THF, from 0 deg C to RT, 14 h 2: 94 percent / NH3, AlMe3 / 1,1,2-trichloro-ethane; toluene / 60 h / Heating 3: 96 percent / Et3N / CH2Cl2 / 2 h / 0 °C 4: 92 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating 5: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 6: Et3N / CH2Cl2 / 24 h / 0 °C 7: tetrahydrofuran / 48 h / 80 °C View Scheme

1: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 2: Et3N / CH2Cl2 / 24 h / 0 °C 3: tetrahydrofuran / 48 h / 80 °C View Scheme

1: 94 percent / NH3, AlMe3 / 1,1,2-trichloro-ethane; toluene / 60 h / Heating 2: 96 percent / Et3N / CH2Cl2 / 2 h / 0 °C 3: 92 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating 4: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 5: Et3N / CH2Cl2 / 24 h / 0 °C 6: tetrahydrofuran / 48 h / 80 °C View Scheme

1: Et3N / CH2Cl2 / 24 h / 0 °C 2: tetrahydrofuran / 48 h / 80 °C View Scheme

1: 96 percent / Et3N / CH2Cl2 / 2 h / 0 °C 2: 92 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating 3: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 4: Et3N / CH2Cl2 / 24 h / 0 °C 5: tetrahydrofuran / 48 h / 80 °C View Scheme

1: 92 percent / NaBH4, tert-butyl alcohol / CH2Cl2 / 70 h / Heating 2: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H2O2 / 1.) THF, 0 deg C, 1 h, 2.) THF, H2O, 0 deg C, 30 min 3: Et3N / CH2Cl2 / 24 h / 0 °C 4: tetrahydrofuran / 48 h / 80 °C View Scheme

in tetrahydrofuran T=80°C; 48 h; Yield given;