Tetrahydro-6-(phenylmethyl)-1H-pyrrolo(3,4-b)pyridine-5,7(2H,6H)-dione → 6-Benzyloctahydro-1H-pyrrolo[3,4-b]pyridine

Participants

Reaction Steps

To a solution of LiAlH4 (1.20 g) in THF was added slowly 6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione (3.00 g) at 0° C. The reaction mixture was refluxed for 6 h under N2, and then cooled to rt. The reaction mixture was quenched with water at 0° C. and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) EA/MeOH) to give the title compound as yellow oil (1.50 g, 47.00%), HPLC: 90.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 217.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.49-1.50 (m, 2H), 1.63-1.66 (m, 2H), 2.76-2.88 (m, 2H), 1.90 (s, 1H), 2.17-2.19 (m, 1H), 2.52-2.63 (m, 4H), 2.74 (t, J=10.4 Hz, 1H), 2.81-2.84 (m, 1H), 2.95-2.98 (m, 1H), 3.21-3.22 (m, J=4.0 Hz), 3.66 (q, J=12.6 Hz, 1H), 7.22-7.34 (m, 5H) ppm.

Provenance & Evidence