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

HRID 1799184

反応式

HRID 1799184 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5d99395cb2e5486a972c2a9bf8993d40
出典データセット
uspto-grants-2013_01
特許番号
US08344028B2

関連ノート

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