HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 59166772, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 3-Chloroaniline | HCID 7932 | — |
| Reactant | 1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate | HCID 4251853 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59166772 | HCID 59166772 | 40.4% |
Reaction Steps
4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (364.5 mg, 1.5 mmol) and 3-chloroaniline (191 mg, 1.5 mmol) were dissolved in DCM (10 ml). To this solution was added sodium triacetoxyborohydride (413 mg, 1.95 mmol) and acetic acid (0.085 ml, 1.5 mmol), and the reaction stirred at room temperature overnight. The reaction mixture was washed with 2N NaOH (5 ml), saturated brine (5 ml), dried over MgSO4 and evaporated. The residue was purified by flash chromatography on silica eluting with DCM to give the title compound as a colourless oil (215 mg, 40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07659305B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-bbb3cb0d846c470497aa145b7bd5ec20 |
| Source note | uspto-grants-2010_02 |