Triethylamine → (3S)-1,3-Dimethyl-2,5-pyrrolidinedione

600 mg (5.26 mmol) of (3S)-3-methyldihydro-2,5-furandione (preparation: S. G. Davies, D. J. Dixon, J. Chem. Soc., Perkin Trans. 1, 1998, 17, 2635-2643) are introduced to a vessel together with 559 mg (0.77 ml, 5.52 mmol) of triethylamine in 5 ml of dichloromethane at 0° C. and 373 mg (5.52 mmol) of methylamine hydrochloride are added. The reaction mixture is stirred at room temperature overnight and then 938 mg (5.78 mmol) of N,N-carbonyldiimidazole are added in portions. The mixture is stirred at room temperature for 1.5 h and at reflux temperature for 30 minutes. After it has cooled to room temperature the reaction mixture is washed with 5% strength hydrochloric acid and water, the organic phase is dried over magnesium sulfate, filtered and concentrated and the product is dried under a high vacuum. This gives 605 mg of the product (88% of theory).

1. stirringThe mixture is stirred at room temperature for 1.5 h
2. temperatureat reflux temperature for 30 minutes
3. temperatureAfter it has cooled to room temperature the reaction mixture
4. washis washed with 5% strength hydrochloric acid and water
5. dry with materialthe organic phase is dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customthe product is dried under a high vacuum

ORD record

ord-25b001f9ed54483c9f82716d2220611f

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402683B2