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

HRID 976516Notes

Reaction equation

HRID 976516 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 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 water
  2. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by column chromatography (eluant: chloroform/ethanol=30/1)

Sources & evidence

ORD record
ord-3b16492e52ce4e93bded553a6c23f86f
Source dataset
uspto-grants-1997_03
Patent number
US05612381

Reaction notes

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