lithium borohydride in methanol; diethyl ether T=0°C; 2 h;

1: 80 percent / silver(I) oxide; tetrabutylammonium iodide / acetonitrile / 12 h / Heating 2: 95 percent / lithium borohydride / methanol; diethyl ether / 2 h / 0 °C View Scheme

1: 73 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C 2: 90 percent / triethylamine; ethanol 3: 80 percent / silver(I) oxide; tetrabutylammonium iodide / acetonitrile / 12 h / Heating 4: 95 percent / lithium borohydride / methanol; diethyl ether / 2 h / 0 °C View Scheme

1: 1.) TsOH, 2.) LiAlH4, AlCl3 / 1.) benzene, reflux, 2.) Et2O, CH2Cl2, reflux 2: TsOH / benzene / Heating View Scheme

1.1: (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol / tetrahydrofuran; water / 102 h / 20 °C 1.2: 0.5 h / 0 - 20 °C 2.1: toluene-4-sulfonic acid / 12 h / 20 °C View Scheme

toluene-4-sulfonic acid in benzene Heating;

toluene-4-sulfonic acid T=20°C; 12 h;

Yield given. Multistep reaction;

Yield given. Multistep reaction;