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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 588276Generated: October 30, 2026

Acetic Acid → HCID 90417432, compound

https://huagongshe.com/reaction/588276

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantTetrahydro-4H-pyran-4-oneHCID 121599—
ReactantHCID 68798350HCID 68798350—
SolventMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
ProductHCID 90417432HCID 9041743295%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09227962B2
Source datasetuspto-grants-2016_01
ORD IDord-df517b7bb95f49938a0cd67c205342c6
Source noteuspto-grants-2016_01