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

HRID 1765995

반응식

HRID 1765995 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-05be860f45ba49bebf97902ddc7e9e71
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07229996B2

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