(Diethylamino)sulfur trifluoride → HCID 57167112, compound

Participants

Reaction Steps

A solution of 4.3 cm3 of diethylaminosulphur trifluoride in 20 cm3 of dry methylene chloride is added dropwise to a solution, cooled to 0° C., of 6.48 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-tert-butoxycarbonyl-perhydroisoindol-4-ol in 70 cm3 of dry methylene chloride. The reaction mixture is stirred at this temperature for 3 hours, washed with 100 cm3 of an aqueous saturated solution of sodium bicarbonate and then with 100 cm3 of an aqueous saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed over a Merck silica gel column (particle size 0.04-0.06 mm, diameter 4.8 cm, height 26 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (95/5 by volume) and collecting fractions of 50 cm3. Fractions 34 to 63 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 2.2 g of (3aS,4S,7aS)-7,7-diphenyl-4-fluoro-4-(2-methoxyphenyl)-2-tert-butoxycarbonyl-perhydroisoindole are obtained in the form of a white foam.

Provenance & Evidence