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

HRID 1091367Notes

Reaction equation

HRID 1091367 reaction equation
C1([C@H]([N:9]2[CH2:14][CH2:13][O:12][C@@H:11]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C@@H:22]4[CH2:26][CH2:25][O:24][CH2:23]4)=[CH:17][CH:16]=3)[CH2:10]2)C)C=CC=CC=1.C([O-])=O.[NH4+].O1CCCC1.CO>[Pd].O>[O:24]1[CH2:25][CH2:26][C@@H:22]([NH:21][C:18]2[CH:17]=[CH:16][C:15]([C@@H:11]3[O:12][CH2:13][CH2:14][NH:9][CH2:10]3)=[CH:20][CH:19]=2)[CH2:23]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 665944544-((1R)-1-phenylethyl)-(2S)-2-(4-(N-((3R)-tetrahydrofuran-3-yl)amino)phenyl)morpholine

Product 1

HCID 66594564(2S)-2-(4-(N-((3R)-tetrahydrofuran-3-yl)amino)phenyl)morpholineYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

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.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b8c1987ebaf545d997f56bc7e6112851
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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