methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate → 3-[5-(methoxycarbonyl)-1H-pyrrol-2-yl]propanoic acid

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Reaction Steps

Methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate (14.8 g, 58.4 mmol) was treated with 4 N HCl (100 mL) at rt for about 12 h. The solvent was removed and the white solid product was dried to give 12.8 g (94%) of 3-(5-(methoxycarbonyl)-1H-pyrrol-2-yl)propanoic acid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.73 (t, J=6.81 Hz, 2H), 2.98 (t, J=6.79 Hz, 2H), 3.83 (s, 3H), 6.01 (dd, J=3.59, 2.61 Hz, 1H), 6.83 (dd, J=3.61, 2.63 Hz, 1H), 9.70 (br s, 1H); LCMS-MS (ESI+) 198.2 (M+H).

Provenance & Evidence