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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 632617Generated: October 31, 2026

Hydrochloric Acid → (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2R)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol

https://huagongshe.com/reaction/632617

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium ChlorideHCID 5234—
ReactantSodium HydroxideHCID 14798—
ReactantHCID 89683079HCID 89683079—
SolventMethanolHCID 887—
Product(5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(2R)-2,3-dihydroxypropyl]oxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-olHCID 7165716999%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of 108.4 mg (0.142 mmol) of (5S)-4-(4,4-Difluorocyclohexyl)-2-[1-(5-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}pyrimidin-2-yl)piperidin-4-yl]-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Reference Example 26, in 2 ml of methanol, 0.5 ml of 2 N hydrochloric acid was added, and the mixture was stirred at 50° C. for 3 hours. After completion of the reaction, 0.5 ml of 2 N sodium hydroxide aqueous solution was added to the reaction solution, then saturated sodium chloride aqueous solution was added, and the reaction solution was extracted with ethyl acetate. The obtained organic phases were combined, washed with saturated sodium chloride aqueous solution, dried with magnesium sulfate and then filtered, and the solvent was distilled off under reduced pressure to provide 101.2 mg of the title compound as a white solid (yield: 99%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09321747B2
Source datasetuspto-grants-2016_04
ORD IDord-c1cfc3fe80bb45dd9d816b68fae34c40
Source noteuspto-grants-2016_04