4-Toluenesulfonyl chloride → HCID 86752416, compound

Participants

Reaction Steps

4.2 g of p-toluenesulphonyl chloride and then 3.1 cm3 of triethylamine are added at room temperature to a solution of 1.17 g of (3aS,4S,6R,7aR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol in 30 cm3 of dichloromethane. The reaction mixture is stirred at this temperature for 18 hours, then washed with twice 25 cm3 of water and then with 25 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 2.8 cm, height 25 cm), eluting under a pressure of 0.8 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60:40 by volume) and collecting fractions of 25 cm3. Fractions 22 to 35 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 0.95 g of (3aS,4S,6R,7aR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-[(S)-2-(2-methoxyphenyl) propionyl]perhydroisoindol-4-ol is obtained in the form of a thick white foam.

Provenance & Evidence