3-Chloro-2-fluorobenzaldehyde → rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-1H-spiro[indole-3,3'-pyrrolidin]-2-one

HRID 2065395노트

반응식

HRID 2065395 반응식
[NH2:1][CH2:2][CH:3]([CH:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:19])[CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6].[Cl:20][C:21]1[C:22]([F:29])=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O>N1C=CC=CC=1>[Cl:18][C:14]1[CH:13]=[C:12]2[NH:11][C:10](=[O:19])[C:9]3([CH:3]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:2][NH:1][CH:24]3[C:23]3[CH:26]=[CH:27][CH:28]=[C:21]([Cl:20])[C:22]=3[F:29])[C:17]2=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 7363353-Chloro-2-fluorobenzaldehydeHCID 58399003Racemic 3-(1-aminomethyl-3,3-dimethyl-butyl)-6-chloro-1,3-dihydro-indol-2-one

생성물 1

HCID 67336394rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-1H-spiro[indole-3,3'-pyrrolidin]-2-one

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

To a solution of racemic 3-(1-aminomethyl-3,3-dimethyl-butyl)-6-chloro-1,3-dihydro-indol-2-one prepared in Example 3 (1.2 g, 4.3 mmol) in pyridine (50 mL) was added 3-chloro-2-fluoro-benzaldehyde (Oakwood) (0.68 g, 4.3 mmol). The reaction mixture was heated at 100° C. for 2 h. The mixture was cooled to room temperature and concentrated. The residue was dissolved into ethyl acetate, washed with aqueous saturated CuSO4 solution, and brine. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by chromatography (50-100% EtOAc in hexanes) to give rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-1H-spiro[indole-3,3′-pyrrolidin]-2-one as a white solid (Yield, 0.29 g, 16%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved into ethyl acetate
  4. washwashed with aqueous saturated CuSO4 solution, and brine
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (50-100% EtOAc in hexanes)
  9. customto give

출처 및 근거

ORD 기록
ord-d93d3b65285946c4bfa249ce08cf1083
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288431B2

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