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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1785245Generated: October 31, 2026

Formaldehyde → 1-methylpiperidin-4-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

https://huagongshe.com/reaction/1785245

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactantpiperidin-4-yl(2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoateHCID 69766623—
CatalystZincchlorideHCID 3007855—
SolventMethanolHCID 887—
SolventEthyl AcetateHCID 8857—
Product1-methylpiperidin-4-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoateHCID 69768513—

Reaction Steps

To a solution of 17 mg of piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate and 0.03 ml of formaldehyde (35% aqueous solution) in 1 ml of methanol, 0.3 ml of advancedly prepared 0.3 M methanol solution of sodium cyanoborohydride and zinc chloride (1:0.5) was added at room temperature, followed by 30 minutes' stirring at the same temperature. The reaction liquid was diluted with ethyl acetate, washed successively with a saturated sodium hydrogencarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 19 mg of the title compound was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07504432B2
Source datasetuspto-grants-2009_03
ORD IDord-58bb9fe142bf4c379013ede835e2d216
Source noteuspto-grants-2009_03