2-Benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione → rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrrole

HRID 1872025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872025
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:21](=O)[CH:20]2[CH:16]([CH2:17][NH:18][CH2:19]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([N:14]1[CH2:15][C@@H:16]2[C@@H:20]([CH2:19][NH:18][CH2:17]2)[CH2:21]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 129585072-Benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dioneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1514450rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrroleAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Lithium aluminium hydride (1M in THF, 85 ml, 85 mmol) was added slowly to a stirred solution of 2-benzyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione (6.4 g, 27.8 mmol) in dry tetrahydrofuran (60 ml) at room temperature under nitrogen. Upon complete addition, the mixture was stirred and heated at 70° C. for 16 h. The mixture was then cooled to 0° C. and carefully quenched with water (3.2 ml), followed by 4N sodium hydroxide (3.2 ml) and water (4.5 ml). The mixture was filtered, washing with ethyl acetate. The filtrate was evaporated and the residue was purified by chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (40:8:1→30:8:1) to give the title amine (4.5 g, 80%) as a clear oil. 1H NMR δ (360 MHz, CDCl3) 2.24-2.28 (2H, m), 2.42 (1H, s), 2.56-2.64 (4H, m), 2.68 (1H, dd, J=11.5. 2.4 Hz), 2.77-2.83 (2H, m), 3.44 (2H, s, CH2Ph), 7.13-7.30 (5H, m, Ar--H). 13C NMR δ (90.5 MHz, CDCl3) 43.6 (CH), 54.4 (CH2), 59.9 (CH2), 60.8 (CH2), 126.8 (CH), 128.2 (CH), 128.8 (CH), 139.3 (C).

Aufarbeitung

  1. additionUpon complete addition
  2. temperatureThe mixture was then cooled to 0° C.
  3. customcarefully quenched with water (3.2 ml)
  4. filtrationThe mixture was filtered
  5. washwashing with ethyl acetate
  6. customThe filtrate was evaporated
  7. customthe residue was purified by chromatography on silica gel
  8. washeluting with CH2Cl2 /MeOH/NH3 (40:8:1→30:8:1)

Quellen und Nachweise

ORD-Eintrag
ord-9ec458e8e8b546989ceaf09f80a0e423
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107321

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