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

HRID 1972187노트

반응식

HRID 1972187 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-2e20e13a73174ad3966116933f724496
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431607B2

반응 노트

불러오는 중…