1: 87 percent / LiN(SiMe3)2 / tetrahydrofuran / -84 °C 2: 96 percent / H2 / Pd/C View Scheme

1: 1) n-butyllithium / 1) THF, -41 deg C, 15 min, 2a) -41 deg C, 1 h, 2b) r.t, 1 h 2: 58.9 percent / triethylamine / methanol / Ambient temperature 3: 50 percent / aq. KOH / aq. ethanol / Ambient temperature View Scheme

1: 1) n-BuLi / 1) THF, hexane, 5 deg C, 2) THF 2: 86 percent / H2 / 5percent Pd/C / ethyl acetate / 2068.6 Torr View Scheme

Multi-step reaction with 2 steps 1: 1) n-butyllithium / 1) THF, -41 deg C, 15 min, 2a) 1h, -41 deg C, 2b) 1-2 h, r.t.2: 65.7 percent / triethylamine / methanol / 18 h / Ambient temperature