HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 2-(6-Tert-butoxycarbonylaminopyridin-3-ylmethylene)-malonic acid diethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Diethyl Malonate | HCID 7761 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | tert-butyl N-(5-formylpyridin-2-yl)carbamate | HCID 22034247 | — |
| Solvent | Heptane | HCID 8900 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | 2-(6-Tert-butoxycarbonylaminopyridin-3-ylmethylene)-malonic acid diethyl ester | HCID 54337991 | 40.3% |
Reaction Steps
To a solution of diethyl malonate (710 μL, 4.7 mmol) and (5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.04 g, 4.7 mmol) in methylene chloride/DMF (1:1, 5 mL) was added piperidine (46 μL, 0.47 mmol) and acetic acid (27 μL, 0.47 mmol). The reaction mixture was stirred for 72 h at room temperature and then for 16 h at 45° C. Heptane was added slowly to give 2-(6-tert-butoxycarbonylaminopyridin-3-ylmethylene)-malonic acid diethyl ester (0.69 g, 40%) as grey crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07071175B1 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-855ca57819ec4d568df1a98193a2fafc |
| Source note | uspto-grants-2006_07 |