HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 90417432, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Tetrahydro-4H-pyran-4-one | HCID 121599 | — |
| Reactant | HCID 68798350 | HCID 68798350 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 90417432 | HCID 90417432 | 95% |
Reaction Steps
To a solution of 5-(piperidin-4-yl)indolin-2-one (64.6 mg, 0.299 mmol) in THF (1.5 ml) and MeOH (3 ml) were added dihydro-2H-pyran-4 (3H)-one (0.132 ml, 1.34 mmol), acetic acid (0.170 ml, 29.5 mmol) and NaBH3(CN) (61.6 mg, 0.931 mmol). After stirring at room temperature for 4 days, the reaction mixture was concentrated. The residue was diluted with sat. NaHCO3 aq. and extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to give 5-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)indolin-2-one (84.9 mg, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09227962B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-df517b7bb95f49938a0cd67c205342c6 |
| Source note | uspto-grants-2016_01 |