Hydrochloric Acid → 7-Chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid

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Reaction Steps

Compound 1b (800 mg, 3.52 mmol) was stirred in a solution of THF (10 mL), MeOH (5 mL), and 1N NaOH (5 mL) at r.t. for 20 h. The solution was made acidic with 1N HCl and extracted (3×) with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo to give 637 mg (85%) of compound 9a as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 13.17 (s, 1H), 6.43 (s, 1H), 3.99 (t, 2H, J=7.4 Hz), 3.32 (t, 2H, J=7.8 Hz), 1.95-2.21 (m, 2H). MS (ES) [m+H] calc'd for C9H8ClNO3, 214. found 214.

Provenance & Evidence