1: 89 percent / NaBH4 / ethanol / 0.5 h 2: 75 percent / aq. KOH / a) reflux, 7 h, b) RT, overnight 3: 81 percent / 5 h / 180 °C 4: 96 percent / borane*THF complex / tetrahydrofuran / 0.5 h / Heating View Scheme

1: 89 percent / NaBH4 / ethanol / 0.5 h 2: 75 percent / aq. KOH / a) reflux, 7 h, b) RT, overnight 3: 81 percent / 5 h / 180 °C View Scheme

1: 89 percent / NaBH4 / ethanol / 0.5 h 2: 75 percent / aq. KOH / a) reflux, 7 h, b) RT, overnight 3: 81 percent / 5 h / 180 °C 4: 96 percent / borane*THF complex / tetrahydrofuran / 0.5 h / Heating 5: 29 percent / N-iodosuccinimide, Ph3P / CH2Cl2 / Ambient temperature View Scheme

piperidine; benzoic acid in toluene 3 h; Heating;

benzoic acid in benzene

sodium tetrahydroborate in ethanol 0.5 h;

1: 89 percent / NaBH4 / ethanol / 0.5 h 2: 75 percent / aq. KOH / a) reflux, 7 h, b) RT, overnight View Scheme