Sodium hydride → 6-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)morpholin-3-one

HRID 1499943Notes

Reaction equation

HRID 1499943 reaction equation
[C:1]([C:4]1[C:5]([O:20][CH3:21])=[C:6]([CH:12]([OH:19])[CH2:13][NH:14][C:15](=[O:18])[CH2:16]Cl)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[H-].[Na+]>O1CCCC1>[C:1]([C:4]1[C:5]([O:20][CH3:21])=[C:6]([CH:12]2[CH2:13][NH:14][C:15](=[O:18])[CH2:16][O:19]2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86677858N-[2-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)-2-hydroxyethyl]-2-chloroacetamide

Product 1

HCID 866778596-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)morpholin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)-2-hydroxyethyl]-2-chloroacetamide (170 mg, 0.50 mmol) (single enantiomer from step 3) in tetrahydrofuran (4 mL) cooled at 0° C., a mixture of sodium hydride (60% dispersion in mineral oil; 39 mg, 1.0 mmol) was added and stirred for 1 hour. The reaction was quenched with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated to give the crude residue as a single enantiomer, 61 mg, 41%. LCMS calculated for C14H17ClNO4 (M+H)+: m/z=298.1; found: 298.1.

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8c9a8103d40b40b783622f461d92dafe
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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