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

HRID 1799184Notes

Reaction equation

HRID 1799184 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 25517Ammonium ChlorideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5d99395cb2e5486a972c2a9bf8993d40
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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