Triethylamine → (4aRS,7aRS)-6-[(2-dimethylaminophenyl)acetyl]-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole

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Reaction Steps

1.18 g of N,N'-carbonyldiimidazole are added to a solution of 1.16 g of 2-dimethylaminophenylacetic acid in 20 cm3 of dry dichloromethane. The mixture is stirred for 30 minutes at +5° C. and then a solution of 2.0 g of (4aRS,7aRS)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole hydrochloride and 1.83 cm3 of triethylamine in 20 cm3 of dichloromethane is added. The reaction mixture is stirred for 1 hour at 20° C. and is then washed twice with 50 cm3 of water and dried over magnesium sulphate. The solution is filtered and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 2.8 cm, height 26 cm), eluting under a nitrogen pressure of 0.6 bar with a cyclohexane and ethyl acetate mixture of (60/40 by volume) and collecting fractions of 60 cm 3 . Fractions 6 to 20 are pooled and concentrated to dryness under reduced pressure (2.7 kPa) and the residue is crystallized from an acetonitrile and diisopropyl oxide mixture. The crystals are drained and dried. 2.16 g of (4aRS,7aRS)-6-[(2-dimethylaminophenyl)acetyl]-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole are obtained in the form of a white solid; melting point 163° C.

Provenance & Evidence