Diethyl aminosulfur trifluoride → HCID 178454071, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 18 g of tert-butyl {trans-4-[2-(2-fluorophenyl)-2-hydroxyethoxy]-cyclohexyl}carbamate in 200 mL of dichloromethane was added over 30 min to a solution of 23 g of diethyl-amino sulfur-trifluoride in 800 mL of dichloromethane cooled to −78° C. under nitrogen atmosphere. The mixture was allowed stir for 1 h at −78° C. then quenched with 100 mL of saturated sodium carbonate. After stirring for 15 min the layers were separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 2%-25% ethyl acetate in hexane gave 12 g of product as a white crystalline solid: 1H NMR (400 MHz, CDCl3) 7.45 (m, 1H), 7.3 (m, 1H), 7.2 (m, 1H), 7.06 (m, 1H), 5.15 (dm, JH-F=48 Hz), 4.18 (br s, 1H), 3.65 (complex m, 2H), 3.42 (br s, 1H), 3.3 (m, 1H), 2.0 (d, 4H), 1.42 (s, 9H), 1.4 (q, 2H), 1.15 (q, 2H).

Provenance & Evidence