1: With dimethylsulfide borane complex in tetrahydrofuran T=60°C; 2 h; 2: With hydrogenchloride in tetrahydrofuran; methanol

lithium aluminium tetrahydride in diethyl ether T=20°C; 16 h;

1: 99 percent / ammonium chloride; 1-hydroxy-7-azabenzotriazole; ethyldiisopropylamine / HOAt / dimethylformamide / 4 h / 20 °C 2: 79 percent / lithium aluminum hydride / diethyl ether / 16 h / 20 °C View Scheme

1: 10.2 g / tetrahydrofuran / 2 h / 0 °C 2: 99 percent / ammonium chloride; 1-hydroxy-7-azabenzotriazole; ethyldiisopropylamine / HOAt / dimethylformamide / 4 h / 20 °C 3: 79 percent / lithium aluminum hydride / diethyl ether / 16 h / 20 °C View Scheme

1: methylmagnesium chloride; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2: 10.2 g / tetrahydrofuran / 2 h / 0 °C 3: 99 percent / ammonium chloride; 1-hydroxy-7-azabenzotriazole; ethyldiisopropylamine / HOAt / dimethylformamide / 4 h / 20 °C 4: 79 percent / lithium aluminum hydride / diethyl ether / 16 h / 20 °C View Scheme