Sodium Hydroxide → (S)-(4-benzylmorpholin-2-yl)methanol

HRID 362959Notes

Reaction equation

HRID 362959 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][O:15]C(=O)C)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54422521(S)-4-benzyl-2-acetoxymethylmorpholine

Product 1

HCID 736507(S)-(4-benzylmorpholin-2-yl)methanolYield 86.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5 g of (S)-4-benzyl-2-acetoxymethylmorpholine was dissolved in 10 ml of ethanol. To the solution was added a solution of 1 g of sodium hydroxide dissolved in 5 ml of water with ice cooling. The mixture was stirred at room temperature for 10 minutes. The reaction mixture was added to 50 ml of ice water and extracted with 50 ml of chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/ethanol=30/1) to obtain 3.6 g of oily (S)-4-benzyl-2-hydroxymethylmorpholine.

Workup

  1. extractionextracted with 50 ml of chloroform
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography (eluant: chloroform/ethanol=30/1)

Sources & evidence

ORD record
ord-81c2de2435794fa7b421e16631437bfa
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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