Ozone → HCID 76568170, 화합물

HRID 1728042노트

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HRID 1728042 반응식
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24](=C)[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1.[O:29]=[O+][O-]>CO.ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24](=[O:29])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 24823OzoneHCID 775802116-chloro-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

생성물 1

HCID 76568170HCID 76568170, 화합물수율 50%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (300 mg, 0.72 mmol) prepared in example 80b in methanol and dichloromethane (1:1, 50 mL) at −78° C. was passed a stream of ozone until the color of the solution turned blue. The reaction mixture was degassed with nitrogen, then methyl disulfide (5 mL) was added. The reaction was slowly warmed to room temperature and stirred overnight. The mixture was concentrated, and the residue was purified by chromatography (EtOAc:CH2Cl2=1:1) to give the racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-propionylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 160 mg, 50%)

후처리

  1. customat −78° C.
  2. customThe reaction mixture was degassed with nitrogen
  3. additionmethyl disulfide (5 mL) was added
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by chromatography (EtOAc:CH2Cl2=1:1)

출처 및 근거

ORD 기록
ord-3b9ea53be4ea454f9c7753a7ff5439b7
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495007B2

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