Sodium hydride → HCID 54311294, compound

HRID 1899840Notes

Reaction equation

HRID 1899840 reaction equation
[H-].[Na+].[CH2:3]([CH:10]1[NH:15][C:14](=[O:16])[CH2:13][O:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH:18]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN(C)C=O>[CH2:3]([CH:10]1[N:15]([CH:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:14](=[O:16])[CH2:13][O:12][CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 16767631HCID 16767631, compoundHCID 54213568HCID 54213568, compound

Product 1

HCID 54311294HCID 54311294, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% NaH (80 mg, 2 mmol) in dry dimethylformamide (8 ml) was added 5-benzyl-3-morpholinone (880 mg, 2 mmol). The mixture was stirred at room temperature for 1 hour. To this were added 4-(3-chloro-3-phenylpropyl)morpholine (480 mg, 2 mmol) and dry dimethylforamide (1 ml). The mixture was then stirred overnight at 60° C. The stirred mixture was placed under reduced pressure to evaporate the solvent. Water was added to the residue, and extraction with ethyl acetate was performed. The extract was washed with a saturated aqueous brine and dried over anhydrous sodium sulfate. The dried extract was placed under reduced pressure to remove the solvent. The oily residue was placed on silica gel column and eluated with ethyl acetate/methanol (20/1) to yield the desired diastereomer A (168 mg, 21.3) and diastereomer B (156 mg, 19.8%).

Workup

  1. stirringThe mixture was then stirred overnight at 60° C
  2. customto evaporate the solvent
  3. additionWater was added to the residue, and extraction with ethyl acetate
  4. washThe extract was washed with a saturated aqueous brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. extractionThe dried extract
  7. customto remove the solvent
  8. customto yield the desired diastereomer A (168 mg, 21.3) and diastereomer B (156 mg, 19.8%)

Sources & evidence

ORD record
ord-148c8c16614d4d82bae78eb8f8bb41a7
Source dataset
uspto-grants-1996_11
Patent number
US05574030

Reaction notes

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