Sodium Chloride → 5-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

A mixture of ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate (11.400 g; 23.68 mmol) and NaCl (2.767 g; 47.36 mmol) in DMSO (111 ml) and water (37 ml) was refluxed, under nitrogen, for 3 h. After cooling to rt, water (150 ml) was added, and the mixture was extracted with AcOEt (3×150 ml). The mixed organic layers were washed with brine (50 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Addition of Et2O and trituration allowed the precipitation of the product. Subsequent filtration, and drying of the obtained solid under HV afforded 5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione as a pink solid. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 410.15 g/mol.

1. temperaturewas refluxed, under nitrogen, for 3 h
2. extractionthe mixture was extracted with AcOEt (3×150 ml)
3. washThe mixed organic layers were washed with brine (50 ml)
4. dry with materialdried over anh. MgSO4
5. filtrationfiltered
6. concentrationconcentrated to dryness under reduced pressure
7. additionAddition of Et2O and trituration
8. customthe precipitation of the product
9. filtrationSubsequent filtration
10. customdrying of the obtained solid under HV

ORD-Eintrag

ord-8e1d897773b54a5eb88f0126f915acbc

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242970B2