HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → Quinoxaline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | N-Boc-cis-4-hydroxy-L-proline methyl ester | HCID 10752873 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Quinoxaline | HCID 7045 | 81% |
Reaction Steps
To the solution of 2-9-2 (0.228 g, 0.745 mmol), (2S,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (0.219 g, 0.894 mmol) and Triphenylphosphine (0.293 g, 1.117 mmol) in THF (3.72 ml), the Diisopropyl azodicarboxylate (0.217 ml, 1.117 mmol) was added dropwise at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was concentrated. The crude product was purified by combiflash (25 g silica gel, 0-40% ethyl acetate in Hexanes) to give 1-1-1 (0.320 g, 0.600 mmol, 81% yield). MS-ESI, m/z=534.45 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08648037B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-4f4ed4ac0bf84b4980af4c7408f0e16c |
| Source note | uspto-grants-2014_02 |