Nitrogen → 1-[4-(4-Chloro-phenoxy)-phenyl]-5-hydroxy-pyrrolidin-2-one

HRID 1972187ノート

反応式

HRID 1972187 の反応式
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C:17](=[O:18])[CH2:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.N#N>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([OH:18])[CH2:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 947NitrogenHCID 14487Diisobutylaluminum hydrideHCID 218348381-[4-(4-Chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione

生成物 1

HCID 594856161-[4-(4-Chloro-phenoxy)-phenyl]-5-hydroxy-pyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-[4-(4-chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione (100 mg, 0.33 mmol) in anhydrous CH2Cl2 (1.5 mL) is cooled down to −78° C. in a dry ice bath. DIBAL-H (0.6 mL, 1 M solution in hexane, 0.66 mmol) is added into the solution dropwise under N2. After the addition, the mixture is stirred at the same temperature for 10 min and quenched by H2O (10 mL). The mixture is warmed up to room temperature and extracted with CH2Cl2 (3×10 mL). The combined organic layer is washed with brine and dried (MgSO4). After filtering the drying agent, the filtrate is concentrated and purified by flash column chromatography (silica gel, EtOAc) to provide the (±)-1-[4-(4-chloro-phenoxy)-phenyl]-5-hydroxy-pyrrolidin-2-one as off white solid (72 mg, 72%).

後処理

  1. additionAfter the addition
  2. customquenched by H2O (10 mL)
  3. extractionextracted with CH2Cl2 (3×10 mL)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtering the drying agent
  7. concentrationthe filtrate is concentrated
  8. custompurified by flash column chromatography (silica gel, EtOAc)

出典と根拠

ORDレコード
ord-2e20e13a73174ad3966116933f724496
出典データセット
uspto-grants-2013_04
特許番号
US08431607B2

反応ノート

読み込み中…