pyrrolidine in methanol 17 h; Ambient temperature;

1: 90 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 2.5 h / Ambient temperature 2: 1.) n-butyllithium / 1.) THF, 0 deg C (0.5 h), -> room temperature (0.25 h), 2.) 0 deg C, 1.5 h View Scheme

1: 1.) n-butyllithium, diisopropylamine / 1.) THF, 0 deg C, 0.5 h, 2.) room temperature 2: lithium aluminum hydride / diethyl ether / 1.75 h / Ambient temperature 3: 90 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 2.5 h / Ambient temperature 4: 1.) n-butyllithium / 1.) THF, 0 deg C (0.5 h), -> room temperature (0.25 h), 2.) 0 deg C, 1.5 h View Scheme

1: lithium aluminum hydride / diethyl ether / 1.75 h / Ambient temperature 2: 90 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 2.5 h / Ambient temperature 3: 1.) n-butyllithium / 1.) THF, 0 deg C (0.5 h), -> room temperature (0.25 h), 2.) 0 deg C, 1.5 h View Scheme

1: pyridine / 0 °C 2: 1) diisopropylamine, butyllithium 3: 97 percent / LiAlH4 / diethyl ether / 0.5 h / Heating 4: 91 percent / PCC, Celite / CH2Cl2 / 2.5 h 5: 1) butyllithium / 1) THF, 0 deg C, 0.5 h, 2) THF, 0 deg C, 1.5 h View Scheme