Dimethyl 3-oxoglutarate → Methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

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Triethylamine (0.5 mL, 3.6 mmol) was added to a mixture of dimethyl 1,3-acetonedicarboxylate (16.3 mL, 111 mmol) and 5-methoxy-3,4-dihydro-2H-pyrrole (10 g, 101 mmol), and the reaction stirred for 72 h. The white solid was collected by filtration, rinsed with ether, and dried under vacuum to give 15.8 g (75%) of compound 1a. 1H NMR (400 MHz, DMSO-d6): δ 11.11 (s, 1H), 5.54 (s, 1H), 3.94 (t, 2H, J=7.6 Hz), 3.80 (s, 3H), 3.36 (t, 2H, J=7.6 Hz), 2.02-2.11 (m, 2H). MS (ES) [m+H] calc'd for C10H11NO4, 210. found 210.

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