1: 71 percent / aq. HCl, charcoal / 1) 25 --> 98 deg C, 2 h; 2) 98 deg C, 2 h 2: 90 percent / sodium borohydride / methanol; acetic acid / 1) below -40 deg C, 1 h; 2) -40 deg C, 3 h; 3) 0 deg C, 18 h 3: 92 percent / formic acid / H2O / 18 h / 80 °C 4: 1.) K2CO3, copper(I) iodide, Ph3P / 1.) Pd/C / 1) DME, water, 25 deg C, 0.5 h; 2) DME, water, reflux, 16 h View Scheme

1: 71 percent / aq. HCl, charcoal / 1) 25 --> 98 deg C, 2 h; 2) 98 deg C, 2 h 2: 90 percent / sodium borohydride / methanol; acetic acid / 1) below -40 deg C, 1 h; 2) -40 deg C, 3 h; 3) 0 deg C, 18 h View Scheme

1: 71 percent / aq. HCl, charcoal / 1) 25 --> 98 deg C, 2 h; 2) 98 deg C, 2 h 2: 90 percent / sodium borohydride / methanol; acetic acid / 1) below -40 deg C, 1 h; 2) -40 deg C, 3 h; 3) 0 deg C, 18 h 3: 92 percent / formic acid / H2O / 18 h / 80 °C View Scheme

hydrogenchloride; carbon 1) 25 --> 98 deg C, 2 h; 2) 98 deg C, 2 h;