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

HRID 1799184

반응식

HRID 1799184 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6212Chloroform용매HCID 25517Ammonium Chloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5d99395cb2e5486a972c2a9bf8993d40
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344028B2

연결된 노트

불러오는 중…