hydrogenchloride; sodium cyanoborohydride in tetrahydrofuran; diethyl ether T=0°C; 0.5 h;

in N,N-dimethyl-formamide; benzyl alcohol T=90°C; 1 h;

1: 1.) sodium hydride / 1.) dioxane, 30 min, reflux, 2.) dioxane, 45 min, reflux 2: 60 percent / sodium cyanoborohydride, hydrogen chloride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C View Scheme

1: 93 percent / dimethylaminopyridine, triethylamine / CH2Cl2; dimethylformamide / 1.) room temperature, 4 h; 2.) 0 deg C, 1 h 2: 89 percent / dimethylformamide; phenylmethanol / 1 h / 90 °C View Scheme

Yield given. Multistep reaction;