HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,3-Cyclopentanedione → (S)-Methyl 2-(tert-butoxycarbonylamino)-3-(3-oxocyclopent-1-enyl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,3-Cyclopentanedione | HCID 77466 | — |
| Reactant | methyl (2R)-2-(((tert-butoxy)carbonyl)amino)-3-iodopropanoate | HCID 10903591 | — |
| Catalyst | Iodine | HCID 807 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-Methyl 2-(tert-butoxycarbonylamino)-3-(3-oxocyclopent-1-enyl)propanoate | HCID 69933833 | 70% |
Reaction Steps
Boc-β-Iodo-Ala-OMe (1.0 g, 3 mmol) was added to a slurry of zinc dust (0.596 g, 9 mmol) and I2 (0.2 mg) in 3 ml DMF under N2. The mixture was stirred for 1 h then Pd2 dba3 (0.070 g, 0.076 mmol), SPhos ligand (0.062 g, 0.15 mmol), and 1,3-cyclopentanedione (0.63 g, 3.9 mmol) were added. The reaction mixture was stirred over night. Purification by flash chromatography (0-100% EtOAc in iso-hexane) gave compound the title compound (0.468 g) in 70% yield. [M+H]+: 284.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815809B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-6190ad954f884631a47b1b3850ec2303 |
| Source note | uspto-grants-2014_08 |