Trifluoroacetic acid → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728095노트

반응식

HRID 1728095 반응식
[Br: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](=[CH2:27])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1.COC([Si](C)(C)C)C.FC(F)(F)C(O)=O>ClCCl>[Br: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](=[CH2:27])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 77581292racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

생성물 1

HCID 76567900racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione수율 81.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (50 mg, 0.08 mmol) prepared in example 161b in dichloromethane (5 mL) was added trifluoroacetic acid (5 mL). The reaction mixture was stirred at room temperature for 0.5 h. After removing the solvent, the residue was dissolved in methanol (2 mL). To the resulting solution was added N,N′-diisopropylethylamine (1 mL). The reaction tube was then heated at 135 ° C. for 20 min. The reaction mixture was concentrated and the residue was purified by Prep-HPLC to obtain racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as solid (30 mg).

후처리

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in methanol (2 mL)
  3. additionTo the resulting solution was added N,N′-diisopropylethylamine (1 mL)
  4. temperatureThe reaction tube was then heated at 135 ° C. for 20 min
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was purified by Prep-HPLC

출처 및 근거

ORD 기록
ord-30d2b1e0e3d341169aeacc8ca961823c
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495007B2

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