1,4-Cyclohexadiene → HCID 86609514, compound

Participants

Reaction Steps

To a solution of 4-benzyl 2-tert-butyl 3-ethyl-5-formyl-1H-pyrrole-2,4-dicarboxylate (1.316 g, 3.682 mmol) in ethanol (15.0 mL) was added 10% palladium on carbon (1.300 g, 3.68 mmol) and 1,4-cyclohexadiene (3.50 mL, 36.82 mmol). The reaction was stirred under N2 for 2 h prior to filtration through a pad of Celite. The filtrate was washed with 50 mL of ethyl acetate and the combined organics concentrated in vacuo. The resultant residue was purified by preparative reverse phase HPLC. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CD3OD) δ 10.23 (s, 1H); 3.10 (q, J=7.3 Hz, 2H); 1.61 (s, 9H); 1.16 (t, J=7.3 Hz, 3H). HRMS (ES) exact mass calculated for C13H17NNaO5 (M+Na+): 290.1001. Found 290.1001.

Provenance & Evidence