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

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

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).

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