1: methyl ester of cyclohexaneacetic acid With N,N'-dimethyl-N,N'-propyleneurea; lithium diisopropyl amide in tetrahydrofuran; hexane T=-78°C; 1 h; 2: ethyl iodide in tetrahydrofuran; hexane T=-78 - 20°C; 14 h;

1.1: 91 percent / H2SO4 / Heating 2.1: LDA; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 95 percent / tetrahydrofuran; hexane / 14 h / -78 - 20 °C View Scheme

P=150012 Torr;

hydrogenchloride

1: 83 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0 - 20 °C 2: 81 percent / PDC; celite / CH2Cl2 / 1 h / 20 °C 3: 88 percent / toluene / Heating 4: 74 percent / H2 / Pd/C / methanol / 20 °C 5: 95 percent / LiOH*H2O; H2O / tetrahydrofuran; ethanol / 20 °C View Scheme