Diethyl aminosulfur trifluoride → HCID 178515020, compound

Participants

Reaction Steps

To a stirred solution of 1 g of trans-2-[4-(2-hydroxy-2-phenyl-ethoxy)-cyclohexyl]-isoindole-1,3-dione in 100 mL of dichloromethane cooled to −78° C. under nitrogen atmosphere was added 1.2 g of diethyl-amino sulfur-trifluoride. The mixture was allowed to warm and stir for 24 h, then quenched with 25 mL of saturated sodium carbonate. After stirring for 15 min, the mixture was diluted with 25 mL of dichloromethane and the layers separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 2%-30% ethyl acetate in hexane gave 0.7 g of product as a white crystalline solid: 1H NMR (400 MHz, CDCl3) 7.8 (m, 2H), 7.7 (t, 1H), 7.4-7.3 (m, 5H), 5.6 (dd, 1H), 4.1 (m, 1H), 3.9-3.65 (complex m, 2H), 3.45 (m, 1H), 2.3 (dd, 2H), 2.2 (m, 2H), 1.8 (d, 2H), 1.4 (dd, 2H).

Provenance & Evidence