Sodium hydride → (5R)-5-Phenylmorpholin-3-one

HRID 1866633Notes

Reaction equation

HRID 1866633 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+].[NH4+].[Cl-]>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

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66972953HCID 66972953, compound

Product 1

HCID 44195698(5R)-5-Phenylmorpholin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-N-[(1R)-2-hydroxy-1-phenylethyl]acetamide from Step A (12.0 g, 56 mmol) in THF (750 mL) at 0° C. was added NaH (4.48 g of a 60% dispersion in oil, 112 mmol) in portions over 1 h and the mixture was stirred at ambient temperature for 1 h. Saturated aqueous NH4Cl (100 mL) was added and the mixture was extracted with EtOAc (2×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=178 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×200 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67cb0d0109aa4703949f3b6e593a1369
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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