Pyridine → HCID 25119929, compound

Participants

Reaction Conditions

Reaction Steps

L-Serine hydantoin (41.4 g, 318 mmol) was suspended in dry MeCN (330 mL) and the solution was cooled to 10° C. Pyridine (88.3 g, 1.11 mol) was added followed by drop wise addition during approx. 1 h of acetyl chloride (87.4 g, 1.11 mol), such that the temperature was maintained at 10° C. After the addition, the reaction was allowed to warm up to 20° C. while a precipitate formed that gradually dissolved. After approx. 16 h, the reaction was complete (as determined by 1H NMR in CDCl3) and was concentrated on the rotavapor at 40° C. to a weight of approx. 240 g during which some solids formed. MTBE (500 mL) was added and more solid precipitated. After stirring for 10 min, the precipitate was collected on a funnel via suction. The cake was washed with additional MTBE (100 mL) and then discarded. The title product resided in the mother liquor. This was concentrated on a rotavapor at 40° C. to thick oil. Weight 73.0 g, ca. 95% purity, approx. 85% yield. 1H NMR: (CDCl3, 300 MHz): δ 4.83 (dd, 1H), 4.73 (t, 1H), 4.44 (dd, 1H), 2.61 (s, 3H), 2.60 (s, 3H), 2.03 (s, 3H).

Provenance & Evidence