METHYL 7-HYDROXY-5-OXO-1,2,3,5-TETRAHYDROINDOLIZINE-8-CARBOXYLATE synthesis

Yield:37704-45-3 75%

Reaction Conditions:

with triethylamine for 72 h;

Steps:

1 Methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (1a)

Methyl 7-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate (1a) 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.

References:

US2009/124595,2009,A1 Location in patent:Page/Page column 33