in dichloromethane T=25°C; 18 h;

hydrogenchloride; lithium borohydride; triethylamine in tetrahydrofuran; methanol

hydrogenchloride; triethylamine in tetrahydrofuran; methanol

sodium borohydride in methanol; ethyl acetate

sodium hydrogencarbonate in tetrahydrofuran; water

hydrogenchloride; triethylamine in tetrahydrofuran; methanol

1: Et3N / tetrahydrofuran / 0.67 h / 0 °C 2: LiBH4 / tetrahydrofuran / 6 h / 0 - 20 °C View Scheme

1: 96 percent / aq. NaOH / 18 h / 80 °C 2: 91 percent / aq. NaOH / tetrahydrofuran View Scheme

1: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT 2: 1.) t-BuOK / 1.) THF, RT, 40 min, 2.) THF, RT, 75 min 3: aq. LiOH / dioxane / 16 h / Ambient temperature 4: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 5: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme