T=23°C; 23 h;

1: H2 / Pd/C / methanol; acetic acid / 4 h / 3102.9 Torr / Ambient temperature 2: 1.) Et3N, MgSO4, 2.) NaBH4 / 1.) MeOH, room temperature, 1.5 h, 2.) MeOH, -5 deg C (1.5 h), 0 deg C (1 h) View Scheme

sodium tetrahydroborate; magnesium sulfate; triethylamine 1.) MeOH, room temperature, 1.5 h, 2.) MeOH, -5 deg C (1.5 h), 0 deg C (1 h); Yield given. Multistep reaction;

in tetrahydrofuran T=20°C; 16 h; Inert atmosphere;

1: 91.1 percent / diisopropylethylamine / dimethylformamide / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h 2: 89.2 percent / H2 / Pd/C / methanol / 4 h / 3102.9 Torr 3: 76.9 percent / aq. Et3N / acetonitrile / 4 h / Ambient temperature View Scheme

palladium 10 on activated carbon; hydrogen P=760.051 Torr; 23 h;

trifluoroacetic acid in dichloromethane 2 h;