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 1728095ノート

反応式

HRID 1728095 の反応式
[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

参加物

4

反応物 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

生成物 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)-dione収率 81.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-30d2b1e0e3d341169aeacc8ca961823c
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

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