dimethylammonium chloride; sodium cyanoborohydride in methanol 2 h; Ambient temperature;

1: 6 N aq. HCl / 0.75 h / Heating 2: MnO2 / CHCl3 / 2 h / 25 °C View Scheme

1: 86 percent / ammonium acetate / 2 h / 100 °C 2: 74 percent / sodium borohydride / methanol / 0.5 h 4: 88 percent / sodium borohydride / methanol / 0.33 h 5: 1.) sodium methoxide, 2.) aq. 20percent titanium trichloride, aq. ammonium acetate / 1.) methanol, 5 min, 2.) room temperature, 45 min 6: 49 percent / sodium cyanoborohydride, dimethylamine hydrochloride / methanol / 2 h / Ambient temperature View Scheme

1: 74 percent / sodium borohydride / methanol / 0.5 h 3: 88 percent / sodium borohydride / methanol / 0.33 h 4: 1.) sodium methoxide, 2.) aq. 20percent titanium trichloride, aq. ammonium acetate / 1.) methanol, 5 min, 2.) room temperature, 45 min 5: 49 percent / sodium cyanoborohydride, dimethylamine hydrochloride / methanol / 2 h / Ambient temperature View Scheme

2: 88 percent / sodium borohydride / methanol / 0.33 h 3: 1.) sodium methoxide, 2.) aq. 20percent titanium trichloride, aq. ammonium acetate / 1.) methanol, 5 min, 2.) room temperature, 45 min 4: 49 percent / sodium cyanoborohydride, dimethylamine hydrochloride / methanol / 2 h / Ambient temperature View Scheme

1: 88 percent / sodium borohydride / methanol / 0.33 h 2: 1.) sodium methoxide, 2.) aq. 20percent titanium trichloride, aq. ammonium acetate / 1.) methanol, 5 min, 2.) room temperature, 45 min 3: 49 percent / sodium cyanoborohydride, dimethylamine hydrochloride / methanol / 2 h / Ambient temperature View Scheme

1: 1.) sodium methoxide, 2.) aq. 20percent titanium trichloride, aq. ammonium acetate / 1.) methanol, 5 min, 2.) room temperature, 45 min 2: 49 percent / sodium cyanoborohydride, dimethylamine hydrochloride / methanol / 2 h / Ambient temperature View Scheme