Water → HCID 67598444, compound

Participants

Reaction Steps

Under argon, 0.77 g (7.1 mmol) of N-methyl-methanesulfonamide was added to a suspension of 0.065 g (2.7 mmol) of 80 percent sodium hydride in 3 ml of DMSO, and the mixture was stirred at RT for 20 min. 1.65 g (5.5 mmol) of (3R,4R)-(+)-6-(4,4,4-trifluorobutoxy)-2,2-dimethyl-3,4-epoxychroman, dissolved in 5 ml of DMSO, were then added dropwise and the batch was left to stand at RT for 4 days and then heated at 45° C. for a further 9 h. The mixture was subsequently poured into water and the precipitate was filtered off with suction and dried thoroughly under reduced pressure, giving 1.9 g of (3R,4S)-(+)-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)chroman-4-yl]-N-methyl-methanesulfonamide, which was recrystallized from a little isopropanol (->1.4 g; m.p. 178-179° C.; optical purity (chiral HPLC) 100%).

Provenance & Evidence