1: With borane-THF in tetrahydrofuran T=20°C; 19 h; Inert atmosphere; 2: With acetic acid in tetrahydrofuran; water

1: 5-Bromo-2-methyl-pyridine With n-butyllithium; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; pentane T=-78°C; 2 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; pentane T=-78 - 0°C; 2.5 h; 3: With methanol; sodium tetrahydroborate in tetrahydrofuran; pentane T=20°C; 0.5 h;

1: With bis-triphenylphosphine-palladium(II) chloride in toluene 2 h; Heating / reflux; 2: With 1,8-diazabicyclo[5.4.0]undec-7-ene in diethyl ether; water 3: With sodium tetrahydroborate; water; ozone more than 3 stages;

1.1: acetic anhydride / 0 - 25 °C 2.1: hydrogenchloride / water / 2 h / Reflux 3.1: borane-THF / tetrahydrofuran / 4 h / 0 - 25 °C / Inert atmosphere 3.2: 0 °C View Scheme

1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 0 - 25 °C 2.1: acetic anhydride / 0 - 25 °C 3.1: hydrogenchloride / water / 2 h / Reflux 4.1: borane-THF / tetrahydrofuran / 4 h / 0 - 25 °C / Inert atmosphere 4.2: 0 °C View Scheme

1.1: hydrogenchloride / water / 2 h / Reflux 2.1: borane-THF / tetrahydrofuran / 4 h / 0 - 25 °C / Inert atmosphere 2.2: 0 °C View Scheme