borane in tetrahydrofuran 1 h;

triethanolamine in tetrahydrofuran; water

1: With borane-THF 2: With sodium hydroxide; dihydrogen peroxide Further stages.;

1.1: 90 percent / H2; AcOH / 10percent Pd/C / 20 °C / 2585.81 Torr 2.1: 92 percent / 1N NaOH / dioxane 3.1: 95 percent / (COCl)2; DMSO / CH2Cl2 / -78 °C 4.1: 40 percent / tetrahydrofuran 5.1: BH3*THF 5.2: 90 percent / H2O2; NaOH View Scheme

1: 87 percent / H2 / PtO2 / H2O; acetic acid / 72 h / 2844.3 Torr 2: Et3N / H2O; dioxane / 96 h 3: 99 percent / BH3 / tetrahydrofuran / 1 h 4: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 5: CH2Cl2 / Ambient temperature 6: 90 percent / H2 / 10percent Pd/C / ethyl acetate 7: 97 percent / NaOH / methanol 8: 98 percent / BH3 / tetrahydrofuran / 1 h View Scheme

1: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 2: CH2Cl2 / Ambient temperature 3: 90 percent / H2 / 10percent Pd/C / ethyl acetate 4: 97 percent / NaOH / methanol 5: 98 percent / BH3 / tetrahydrofuran / 1 h View Scheme

1: CH2Cl2 / Ambient temperature 2: 90 percent / H2 / 10percent Pd/C / ethyl acetate 3: 97 percent / NaOH / methanol 4: 98 percent / BH3 / tetrahydrofuran / 1 h View Scheme

1: 99 percent / BH3 / tetrahydrofuran / 1 h 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 3: CH2Cl2 / Ambient temperature 4: 90 percent / H2 / 10percent Pd/C / ethyl acetate 5: 97 percent / NaOH / methanol 6: 98 percent / BH3 / tetrahydrofuran / 1 h View Scheme

1: 90 percent / H2 / 10percent Pd/C / ethyl acetate 2: 97 percent / NaOH / methanol 3: 98 percent / BH3 / tetrahydrofuran / 1 h View Scheme

1: Et3N / H2O; dioxane / 96 h 2: 99 percent / BH3 / tetrahydrofuran / 1 h 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 4: CH2Cl2 / Ambient temperature 5: 90 percent / H2 / 10percent Pd/C / ethyl acetate 6: 97 percent / NaOH / methanol 7: 98 percent / BH3 / tetrahydrofuran / 1 h View Scheme