N-bromobutanimide → (4R)-4-(3-Amino-6-bromo-4-chlorophenyl)pyrrolidin-2-one

HRID 1799184

Reaktionsgleichung

Reaktionsgleichung von HRID 1799184
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(O)(=O)C.[Cl-].[NH4+]>[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)[C:5]([Br:15])=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 66724932(4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one

Produkt 1

HCID 66724936(4R)-4-(3-Amino-6-bromo-4-chlorophenyl)pyrrolidin-2-oneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Seven and one-half (7.5) g (35.71 mmol) of (4R)-4-(3-amino-4-chlorophenyl)-pyrrolidin-2-one was dissolved in 170 mL chloroform (0.25 M) and 3 mL of acetic acid. To this solution, 6.3 g of solid N-bromosuccinimide was added portion-wise. The reaction was stirred overnight at room temperature. The reaction mixture was diluted with saturated ammonium chloride aqueous solution (50 mL). The aqueous solution was extracted with dichloromethane (2×50 mL), dried over MgSO4 and the solvent evaporated to dryness. Water was added to the oil and the pH adjusted to 9 with 1N NaOH. The solid was filtered, washed consecutively with water, ether, and hexane and dried under a high vacuum to give 9.3 g of the title compound (88% yield).

Aufarbeitung

  1. extractionThe aqueous solution was extracted with dichloromethane (2×50 mL)
  2. dry with materialdried over MgSO4
  3. customthe solvent evaporated to dryness
  4. additionWater was added to the oil
  5. filtrationThe solid was filtered
  6. washwashed consecutively with water, ether, and hexane
  7. customdried under a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5d99395cb2e5486a972c2a9bf8993d40
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344028B2

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