chromic acid in acetone T=0°C; 8 h;

1: 1.) n-BuLi, 3.) conc. HCl, 4.) aq. NaOH 2: 100 percent / Zn, AcOH / 24 h / Heating 3: 99 percent / ZnCl2 / acetic acid / 2 h / Heating 4: 99 percent / Na2Cr2O7*H2O / acetic acid / 1 h / Heating 6: 1.) HCl, 2.) NaBH4 / 2.) DMSO 7: 94 percent / HBr, HOAc / 3.5 h / Heating View Scheme

1: 88.6 percent / piperidine acetate / toluene / Heating 2: 90 percent / LiAlH4 / tetrahydrofuran / Heating 3: 50percent aq. sulphuric acid / a. water removed, b. 130-140 deg C (15mm), 2h 4: 10percent aq. NaOH / Heating 5: 82.3 percent / Heating 6: POCl3 / toluene / 95 °C 7: NaBH4 / methanol / Ambient temperature View Scheme

piperidinium acetate in toluene Heating;

1: 94 percent / 2.67 M chromic acid / acetone / 8 h / 0 °C 2: 71 percent / Et3N, diphenylphosphoryl azide / dioxane / 5 h / Heating 3: 100 percent / H2 / 5percent Pd/C / methanol / 1 h View Scheme

ethyl mercaptan sodium salt in N,N-dimethyl-formamide 0.333333 h; Heating;