Sodium borohydride → N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

To a THF (6 ml) solution of 1-(1,3-benzothiazol-6-yl)ethanone (European Journal of Organic Chemistry (1998), (9), 2047-2050., 250 mg, 1.41 mmol) and (R)-(+)-2-methyl-2-propane sulfinylamide (188 mg, 1.55 mmol), titanium(IV) ethoxide (2 ml) was added and the mixture was stirred for 40 minutes at 85° C. under microwave condition. The mixture was then cooled to 0° C. and sodium borohydride (188 mg, 5.0 mmol) was added to the reaction mixture. After stirring for 2 hours at the temperature, the reaction was partitioned with water and EtOH followed by stirring for 1 hour at room temperature. Then, filtration, evaporation gave N-[1-(1,3-benzothiazol-6-yl)ethyl]-2-methylpropane-2-sulfinamide (MS (ESI) m/z 281 (M−H)−, 283 (M+H)+) which was then added hydrochloric acid-MeOH (2.0 M, 7.0 ml) and 1,4-dioxane (7.0 ml). The mixture was then stirred for 1.5 hours at room temperature and the same reaction procedure as Example 14 was performed to give the title compound. MS (ESI) m/z 180 (M−H)+

Provenance & Evidence