Potassium Sodium Tartrate → N-methoxy-N,2-dimethyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide

Participants

Reaction Steps

A solution of N-methoxymethanamine hydrochloride (1.00 g) in toluene (10 mL) was cooled to 0° C., and trimethylaluminum (1.4M hexane solution, 7.36 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 1.5 hr, and a solution (10 mL) of ethyl 2-methyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate (1.11 g) in toluene was added dropwise thereto. The reaction mixture was stirred at room temperature for 24 hr, saturated aqueous sodium hydrogen carbonate and saturated aqueous Rochelle salt solution were added and the mixture was stirred for 1 hr. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (401 mg, yield 35%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio).

Provenance & Evidence