Water → HCID 53859425, compound

HRID 1899833Notes

Reaction equation

HRID 1899833 reaction equation
[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.[Na].O>C(O)C>[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH:16]([OH:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 54254428HCID 54254428, compound2×HCID 178418435HCID 178418435, compound

Product 1

HCID 53859425HCID 53859425, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Benzyl-3-(3-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one (0.31 g, 1 mmol) prepared in the above (1) was dissolved in 3 ml of ethanol. To the solution, sodium boron hydride (80 mg, 2 mmol) was added under stirring while chilling with ice. After the resulting solution was stirred to cause reaction at room temperature for 30 minutes, water was added. The obtained solution was extracted with ethyl acetate. The organic portion was sequentially washed with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure to obtain 0.31 g of the titled compound as a colorless oil (yield: 100%).

Workup

  1. temperaturewhile chilling with ice
  2. stirringAfter the resulting solution was stirred
  3. customreaction at room temperature for 30 minutes
  4. extractionThe obtained solution was extracted with ethyl acetate
  5. washThe organic portion was sequentially washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-039578829cf54601bca0ebf8cf947a54
Source dataset
uspto-grants-1996_11
Patent number
US05574030

Reaction notes

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