1H-1,2,4-triazol; 1,8-diazabicyclo[5.4.0]undec-7-ene in chloroform-d1 24 h; Reflux;

1: lithium hydroxide hydrate / tetrahydrofuran; water / 48 h / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere View Scheme

1: With sodium hydroxide; isopropyl alcohol T=20°C; 6 h; 2: With hydrogenchloride; water

hydrogen in methanol T=160°C; P=150015 Torr; Product distribution / selectivity;

1.1: sodium tetrahydroborate / tetrahydrofuran / |Inert atmosphere; |Reflux 1.2: 9 h / 60 - 65 °C / |Inert atmosphere 2.1: iodine; triphenylphosphine; 1H-imidazole / dichloromethane / 2 h / 20 - 35 °C 3.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 1.17 h / 20 °C / |Inert atmosphere 3.2: 6.25 h / 20 °C / |Inert atmosphere 4.1: hydrogenchloride / water; tert-butyl methyl ether / 20 °C View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran / |Inert atmosphere; |Reflux 1.2: 9 h / 60 - 65 °C / |Inert atmosphere 2.1: hydrogen bromide / water / 15 h / 85 - 90 °C View Scheme

1: lithium hydroxide hydrate / tetrahydrofuran; water / 48 h / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / diethyl ether / 5 h / Reflux View Scheme

1: With diisobutylaluminium hydride in hexane; toluene T=-80 - -78°C; 2.5 h; 2: With methanol in hexane; toluene T=-80 - -78°C;

hydrogenchloride in hexane; dichloromethane; water

1.1: N-BuLi / tetrahydrofuran / 0 °C 1.2: 80 percent / tetrahydrofuran 2.1: NaHMDS / 1,2-dimethoxy-ethane 2.2: 50 percent / 1,2-dimethoxy-ethane 3.1: (S)-BINAL-H; LiAlH4 / tetrahydrofuran 4.1: K2CO3; MeOH 5.1: p-TSA / CH2Cl2 6.1: DIBAL-H / -78 °C 7.1: NaHMDS 8.1: aq. AcOH / tetrahydrofuran View Scheme