HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 723644Generated: October 25, 2026
Dimethyl acetylenedicarboxylate → 7-Azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid 2,3-dimethyl 7-tert-butyl ester
https://huagongshe.com/reaction/723644
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl acetylenedicarboxylate | HCID 12980 | — |
| Reactant | tert-butyl 1H-pyrrole-1-carboxylate | HCID 643494 | — |
| Product | 7-Azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid 2,3-dimethyl 7-tert-butyl ester | HCID 14085413 | 50% |
Reaction Steps
Freshly distilled acetylenedicarboxylic acid dimethyl ester (6.7 mL, 54 mmol) and N-(tert-butyloxycarbonyl)-1H-pyrrole (9.0 mL, 54 mmol) were combined and heated at 120° C. for 3 h. Purification by flash chromatography on SiO2 eluting with EtOAc/CH2Cl2 gave 8.3 g (27 mmol, 50%) of compound 31A as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07141578B2 |
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| Source dataset | uspto-grants-2006_11 |
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| ORD ID | ord-cf73406a75374ce68bddf715f69afaa4 |
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| Source note | uspto-grants-2006_11 |
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