1: Raney nickel; diethyl ether / Hydrogenation View Scheme

1: 72 percent / lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C 2: 14.06 g / LiAlH4 / diethyl ether / a.) 0 deg C, 10 min, b.) room temperature, 3.5 h 3: 83 percent / Et3N, DMAP / CH2Cl2 / 20 h / Ambient temperature 4: 91 percent / H2 / 10percent Pd-C / ethanol / Ambient temperature 5: H2O; propan-2-ol / pig pancreatic lipase, pH 7 buffer (K2HPO4-KH2PO4) View Scheme

ethanol; nickel Hydrogenation;

P=73550.8 - 95616 Torr; Hydrogenation;

P=73550.8 - 95616 Torr; Hydrogenation;

piperidinium acetate in benzene Heating;

in dichloromethane Ambient temperatureIrradiation;

BuTeBu 2 h; Ambient temperature;