Potassium Carbonate → (S)-N-[5-(1,2-dihydroxy-ethyl)-pyrazin-yl]-2,2-dimethyl-propionamide

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium ferricyanide (148.74 g, 450 mmol), potassium carbonate (62.25 g, 450 mmol), and (DHQ)2PHAL (2.6 g, 3.34 mmol) was treated with a solution of water/tert-butyl alcohol (2 L, 1:1), and the reaction mixture was stirred at 25° C. for 15 min. The reaction mixture was cooled to 5° C., treated with a 0.2M solution of osmium tetroxide in toluene (7.5 mL, 1.5 mmol), and then treated with 2,2-dimethyl-N-(5-vinyl-pyrazin-2-yl)-propionamide (30.8 g, 150 mmol) which was partially dissolved in water/tert-butyl alcohol (150 mL, 1:1). The mixture was stirred at 4–5° C. for 18 h using a Neslab Endocal cooling system to control the temperature. While stirring at 4–5° C., the mixture was then slowly treated with sodium metabisulfite (35 g, 184 mmol) which resulted in effervescence. The cooling bath was removed, and the stirring continued for 15 min. The layers were separated, and the aqueous layer was extracted with ethyl acetate (600 mL). Each organic layer was washed with a saturated aqueous sodium chloride solution (500 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford N-[5-(1(S),2-dihydroxy-ethyl)-pyrazin-2-yl]-2,2-dimethyl-propionamide (46 g, 100%) as a red oil which was used without further purification.

Provenance & Evidence