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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1091367Generated: November 1, 2026

Methanol → (2S)-2-(4-(N-((3R)-tetrahydrofuran-3-yl)amino)phenyl)morpholine

https://huagongshe.com/reaction/1091367

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantTetrahydrofuranHCID 8028—
ReactantAmmonium formateHCID 2723923—
Reactant4-((1R)-1-phenylethyl)-(2S)-2-(4-(N-((3R)-tetrahydrofuran-3-yl)amino)phenyl)morpholineHCID 66594454—
CatalystPalladiumHCID 23938—
SolventWaterHCID 962—
Product(2S)-2-(4-(N-((3R)-tetrahydrofuran-3-yl)amino)phenyl)morpholineHCID 66594564103.4%

Reaction Conditions

Temperature95 °C

Reaction Steps

To a solution of 4-((1R)-1-phenylethyl)-(2S)-2-(4-[N-{(3R)-tetrahydrofuran-3-yl}amino]phenyl)morpholine (0.40 g, 1.09 mmol) and ammonium formate (0.69 g, 10.9 mmol) in mixture of tetrahydrofuran (50 ml), methanol (100 ml) and water (16 ml) was added 10% palladium on carbon (wet, 150 mg) and stirred at 95° C. for one hour. After filtration, the solvent was removed in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give (2S)-2-[4-{N-((3R)-tetrahydrofuran-3-yl)amino}phenyl]morpholine (0.28 g, quant.) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08129377B2
Source datasetuspto-grants-2012_03
ORD IDord-b8c1987ebaf545d997f56bc7e6112851
Source noteuspto-grants-2012_03