Tetrahydrofuran → N-[(1R)-1-(6-methylpyridin-3-yl)ethyl]-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

To a THF (25 ml) solution of 1-(6-methylpyridin-3-yl)ethanone (2.1 g, 15.5 mmol), (R)-(+)-2-methyl-2-propanesulfinylamide (2.26 g, 18.6 mmol) and titanium(IV) ethoxide (25 ml) were added and the mixture was stirred for 24 hours at 70° C. Then, the mixture was cooled to 0° C. and sodium borohydride (2060 mg, 54 mmol) was added. After stirring for 2 hours, water and EtOH were added to the mixture with stirring for 1 hour at room temperature. Filtration, evaporation gave N-[(1R)-1-(6-methylpyridin-3-yl)ethyl]-2-methylpropane-2-sulfinamide which was treated with hydrochloric acid-MeOH (2.0 M, 15.0 ml) and 1,4-dioxane (15.0 ml) for 1.5 hours at room temperature. Then, the reaction mixture was evaporated and diethyl ether was added to form a precipitate, which was collected, washed with diethyl ether to give (1R)-1-(6-methylpyridin-3-yl)ethanamine hydrochloride (2.12 g, 28%). MS (ESI) m/z 161 (M−H)−.

Provenance & Evidence