Trifluoroacetic acid → 2,5-Dibenzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

HRID 1765995

反応式

HRID 1765995 の反応式
[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH2:17][N:18]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:19][Si](C)(C)C.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]2[CH:10]([CH2:17][N:18]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19]2)[C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 74204BenzylmaleimideHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

生成物 1

HCID 218676822,5-Dibenzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione収率 72.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

N-Benzylmaleimide (5.0 g, 26.7 mmol), and N-(methoxymethyl)-N-(trimethylsilylmethyl) benzylamine (7.0 g, 29.4 mmol) were dissolved in toluene (150 mL). Trifluoroacetic acid (500 μL, 6.5 mmol) was added at room temperature. The reaction was allowed to stir for two hours at room temperature, and the precipitate was filtered off (˜440 mg). The filtrate was concentrated and purified by silica gel column chromatography (20-50% ethyl acetate in hexanes) to afford a white solid (6.2 g, 72%). 1H NMR (400 MHz, CDCl3): δ 7.22-7.05 (m, 8H), 7.01-6.96 (m, 2H), 4.45 (s, 2H), 3.95 (s, 2H), 3.50 (d, J=11.0 Hz), 3.37 (d, J=8.8 Hz), 3.10 (app t, J=9.1 Hz); 13C NMR (400 MHz, CDCl3): δ 175.8 (C═O), 134.8 (Ph), 130.6 (Ph), 129.6 (Ph), 129.3 (Ph), 128.8 (Ph), 128.6 (Ph), 128.3 (Ph), 127.7 (Ph), 57.3 (CH2), 54.0 (CH2), 42.9 (CH), 42.6 (CH2).

後処理

  1. filtrationthe precipitate was filtered off (˜440 mg)
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography (20-50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-05be860f45ba49bebf97902ddc7e9e71
出典データセット
uspto-grants-2007_06
特許番号
US07229996B2

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