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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 710046Generated: October 29, 2026

Phenol → (S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl)ethanone

https://huagongshe.com/reaction/710046

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhenolHCID 996—
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactant(S)-(5-(1-(2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetyl)pyrrolidin-2-yl)-1,3,4-oxadiazol-2-yl)methyl methanesulfonateHCID 86706759—
SolventWaterHCID 962—
Product(S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl)ethanoneHCID 6020271497.6%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a DMF (1.0 mL) solution of the compound (32.5 mg) obtained in Example 9-(6) and phenol (13 mg), K2CO3 (37 mg) was added and the mixture was stirred at 50° C. for 3.5 hours. The reaction mixture was added to water (20 mL) and the organic layer extracted with AcOEt (20 mL×2) was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (31.6 mg, colorless amorphous.)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09181229B2
Source datasetuspto-grants-2015_11
ORD IDord-2a6c891141924db0aa5504d315b12518
Source noteuspto-grants-2015_11