HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 59333649, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | 2,6-Dichloropurine | HCID 5324412 | — |
| Reactant | tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate | HCID 6544479 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59333649 | HCID 59333649 | 92.2% |
Reaction Steps
Tetrahydrofuran (200 ml) was added to 2,6-dichloropurine (6 g, 31.8 mmol), tert-butyl(3R)-3-hydroxypyrrolidine-1-carboxylate (5.94 g, 31.8 mmol), and triphenylphosphine (9.2 g, 34.9 mmol) and the resulting mixture was made uniform. Diisopropyl azodicarboxylate (6.9 ml, 35 mmol) was added with ice cooling and the resulting mixture was stirred at room temperature for 30 minutes and then heated to reflux for 1 hour. The reaction mixture was cooled, then the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3 to 6:4 to 5:5 to 4:6) to give the title compound (10.5 g, 92%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08097622B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-9218a60ef0cf453393027598e4504fde |
| Source note | uspto-grants-2012_01 |