4-(N,N-dimethlyamino)pyridine in dichloromethane T=20°C; Inert atmosphereCooling with ice;

1: piperidine / benzene / Ambient temperature 2: 68 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 90 percent / pyridine / diethyl ether / -15 °C 4: CaCO3 / CH2Cl2 / Ambient temperature 5: t-BuOK / dimethylsulfoxide-d6 / 1 h / 20 °C View Scheme

1: 90 percent / pyridine / diethyl ether / -15 °C 2: CaCO3 / CH2Cl2 / Ambient temperature 3: t-BuOK / dimethylsulfoxide-d6 / 1 h / 20 °C View Scheme

1: 68 percent / NaBH4 / methanol / 2 h / Ambient temperature 2: 90 percent / pyridine / diethyl ether / -15 °C 3: CaCO3 / CH2Cl2 / Ambient temperature 4: t-BuOK / dimethylsulfoxide-d6 / 1 h / 20 °C View Scheme

1: CaCO3 / CH2Cl2 / Ambient temperature 2: t-BuOK / dimethylsulfoxide-d6 / 1 h / 20 °C View Scheme

1: With trimethylsilyl bromide in dichloromethane T=20°C; 2 h; 2: With methanol; ammonia in dichloromethane