HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-((1R,4R,5S,8S,12R)-4-methyl-2,6-dioxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-7-yl)-2-(trifluoromethyl)benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | Benzonitrile, 4-((3aR,4S,6R,6aS,8aS,8bR)-octahydro-4-hydroxy-6-methyl-7-oxo-3a,6-epoxy-3ah-pyrano(2,3,4-cd)isoindol-8(4H)-yl)-2-(trifluoromethyl)- | HCID 59635881 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-((1R,4R,5S,8S,12R)-4-methyl-2,6-dioxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-7-yl)-2-(trifluoromethyl)benzonitrile | HCID 59636059 | 97.3% |
Reaction Steps
Dess-Martin periodinane (12 g, 28.3 mmol) was added to a solution of Example 3 (3.0 g, 7.6 mmol) in THF (20 mL) and CH2Cl2 (30 mL) at room temperature. The reaction mixture was stirred at room temperature for 18 h and CH2Cl2 (50 mL), aq. 15% Na2S2O3 solution (25 mL), and aq. 2M Na2CO3 solution (25 mL) were added. The mixture was stirred for 1 h and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 2.9 g (97%) of the Example 5.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08067582B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-8a46be3b7eed478d9ea60b876fa52b5a |
| Source note | uspto-grants-2011_11 |