1: 1) H2; 2) NaH / 1) 10percent Pt-C / 1) THF, 5 h, 59 -> 27 lb/square inch; 2) THF, reflux, 5 h 2: 81 percent / KOH / ethanol / 14 h / Heating 3: 84 percent / Ac2O / 2 h / Heating View Scheme

1: 93 percent / piperidine, HOAc / benzene / 14 h / Heating 2: 1) H2; 2) NaH / 1) 10percent Pt-C / 1) THF, 5 h, 59 -> 27 lb/square inch; 2) THF, reflux, 5 h 3: 81 percent / KOH / ethanol / 14 h / Heating 4: 84 percent / Ac2O / 2 h / Heating View Scheme

acetic anhydride 2 h; Heating;

1: 81 percent / KOH / ethanol / 14 h / Heating 2: 84 percent / Ac2O / 2 h / Heating View Scheme

titanium tetrachloride in dichloromethane 1 h; Ambient temperature;