Sodium hydride → (5S)-5-Phenyl-3-morpholinone

HRID 595972Notes

Reaction equation

HRID 595972 reaction equation
Cl[CH2:2][C:3]([NH:5][C@@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][OH:8])=[O:4].[H-].[Na+]>C1COCC1>[C:9]1([C@@H:6]2[NH:5][C:3](=[O:4])[CH2:2][O:8][CH2:7]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21861287HCID 21861287, compound

Product 1

HCID 11105904(5S)-5-Phenyl-3-morpholinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-chloro-N-(2-hydroxy-1-phenylethyl)acetamide (600 mg, 2.8 mmol) in anhydrous THF solution at 0° C. was added NaH mineral oil suspension (247 mg, 6.18 mmol). The resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated to dryness, and the residue was partitioned between CH2Cl2/brine/H2O (20 mL/18 mL/2 mL). CH2Cl2 layer was dried over anhydrous Na2SO4, filtered off, concentrated in vacuo. The crude product, (S)-5-phenylmorpholin-3-one, was obtained as a white solid (498 mg, 97%). The crude product was used directly in next step without further purification. LCMS (m/z): 178.2 (MH+), 0.47 min.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was partitioned between CH2Cl2/brine/H2O (20 mL/18 mL/2 mL)
  3. dry with materialCH2Cl2 layer was dried over anhydrous Na2SO4
  4. filtrationfiltered off
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a122641fff0b4ee09144ab386dd059fa
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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