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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2103410Generated: October 31, 2026

Ethyl Acetate → 1-(5-Pyrimidin-2-ylpyridin-2-yl)-4-{[(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-yl]amino}cyclohexanol

https://huagongshe.com/reaction/2103410

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-amineHCID 57803297—
Reactant4-Hydroxy-4-[5-(2-pyrimidinyl)-2-pyridyl]cyclohexanoneHCID 57803358—
SolventMethanolHCID 887—
SolventIsopropanolHCID 3776—
Product1-(5-Pyrimidin-2-ylpyridin-2-yl)-4-{[(3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-yl]amino}cyclohexanolHCID 11157181—

Reaction Steps

To a solution of (3S)-1-({[4-(trifluoromethyl)pyridin-2-yl]methoxy}acetyl)pyrrolidin-3-amine (47 mg, 0.15 mmol) and 4-hydroxy-4-(5-pyrimidin-2-ylpyridin-2-yl)cyclohexanone (41 mg, 0.15 mmol) in methanol (2 mL) and isopropanol (2 mL) was added sodium triacetoxyborohydride (36 mg, 0.17 mmol). After being stirred at room temperature overnight, EtOAc was added. The solution was washed with NaHCO3 solution and water, dried (MgSO4) and concentrated. Purification by HPLC provided two isomers of the title compound. MS (M+H) 557.2 for both isomers.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07576089B2
Source datasetuspto-grants-2009_08
ORD IDord-dc02889d3cf742cb844ebc71ad86072e
Source noteuspto-grants-2009_08