Diisopropylethylamine → HCID 67661897, compound

Participants

Reaction Conditions

Reaction Steps

0.87 cm3 of diisopropylethylamine, 0.75 g of (S)-2-phenylpropionic acid, 0.02 g of hydroxybenzotriazole hydrate and 1.05 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added to a solution of 1.43 g of (3aS,4S,6S,7aR)-6-cyanomethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol in 20 cm3 of dichloromethane. The reaction mixture is stirred at 20° C. for 20 hours and then washed twice with 30 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is chromatographed on a silica gel column (particle size 0.04-0.063 mm, height 32 cm, diameter 2.8 cm), eluting under a pressure of 0.6 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50:50 by volume) and collecting fractions of 25 cm3. Fractions 19 to 35 are concentrated to dryness under reduced pressure (2.7 kPa). 1.20 g of (3aS,4S,6S,7aR)-6-cyanomethyl-4-(2-methoxyphenyl)-2-[(S)-2-phenylpropionyl]perhydroisoindol-4-ol in the form of a thick white foam are obtained.

Provenance & Evidence