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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2367055Generated: 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/2367055

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 numberUS08697870B2
Source datasetuspto-grants-2014_04
ORD IDord-771d67ed8de1465fae32a0b6be363278
Source noteuspto-grants-2014_04