Dimethyl acetylenedicarboxylate → HCID 11109638, compound

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Reaction Conditions

Reaction Steps

A mixture of tert-butyl 1H-pyrrole-1-carboxylate (XLV) (3.50 g 20.93 mmol), dimethyl but-2-ynedioate (XLVI) (2.57 mL, 20.93 mmol) and AlCl3 (28 mg, 0.21 mmol) were stirred for 3 days at 70° C. The crude product was purified by silica gel chromatography using 100% DCM then DCM/MeOH 1000/1→500/1 to give (1R,4S)-7-tert-butyl 2,3-dimethyl 7-azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylate (XLVII) as a yellow oil (3.41 g, 11.04 mmol, 53% yield). 1H NMR (CDCl3) δ ppm 1.40 (s, 9H), 3.80 (s, 6H), 5.44 (s, 2H), 7.13 (d, J=13 Hz, 2H); ESIMS found for C15H19NO6 m/z 332 (M+Na).

Provenance & Evidence