sodium hydroxide in methanol 2 h; Heating;

1: 85 percent / diisopropylethylamine / dimethylformamide / 3 h / 91 - 94 °C 2: 100 percent / NaBH4 / methanol; tetrahydrofuran / 2 h / 0 °C 3: 95 percent / Et3SiH, TFA / 1.) 0 deg C, 1.5 h, 2.) RT, overnight 4: 80 percent / H2 / PtO2 / ethyl acetate / 1.25 h / 2068.6 Torr 5: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu2O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h 6: 87 percent / K2CO3 / dimethylformamide / Ambient temperature 7: 70 percent / aq. NaOH / methanol / 2 h / Heating View Scheme

1: 80 percent / H2 / PtO2 / ethyl acetate / 1.25 h / 2068.6 Torr 2: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu2O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h 3: 87 percent / K2CO3 / dimethylformamide / Ambient temperature 4: 70 percent / aq. NaOH / methanol / 2 h / Heating View Scheme

1: 100 percent / NaBH4 / methanol; tetrahydrofuran / 2 h / 0 °C 2: 95 percent / Et3SiH, TFA / 1.) 0 deg C, 1.5 h, 2.) RT, overnight 3: 80 percent / H2 / PtO2 / ethyl acetate / 1.25 h / 2068.6 Torr 4: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu2O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h 5: 87 percent / K2CO3 / dimethylformamide / Ambient temperature 6: 70 percent / aq. NaOH / methanol / 2 h / Heating View Scheme

1: 95 percent / Et3SiH, TFA / 1.) 0 deg C, 1.5 h, 2.) RT, overnight 2: 80 percent / H2 / PtO2 / ethyl acetate / 1.25 h / 2068.6 Torr 3: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu2O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h 4: 87 percent / K2CO3 / dimethylformamide / Ambient temperature 5: 70 percent / aq. NaOH / methanol / 2 h / Heating View Scheme

1: 1.) 48percent aq. HBr, sodium nitrite, 2.) Cu2O / 1.) acetone, methanol, from 0 to 5 deg C, 15 min, 2.) acetone, methanol, 1 h 2: 87 percent / K2CO3 / dimethylformamide / Ambient temperature 3: 70 percent / aq. NaOH / methanol / 2 h / Heating View Scheme

1: 87 percent / K2CO3 / dimethylformamide / Ambient temperature 2: 70 percent / aq. NaOH / methanol / 2 h / Heating View Scheme