1,4-Dioxane → (S)-3-Hydroxy-4-morpholin-4-yl-4-oxo-butyric acid methyl ester

HRID 1796150Notes

Reaction equation

HRID 1796150 reaction equation
C([O:4][C@H:5]([C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])[CH2:6][C:7]([OH:9])=[O:8])(=O)C.[C:18](OC(CC(N1CCOCC1)=O)C(O)=O)(=O)C.O1CCOCC1.C([O-])(O)=O.[Na+]>CO>[CH3:18][O:9][C:7](=[O:8])[CH2:6][C@H:5]([OH:4])[C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 220540362-Acetoxy-4-morpholin-4-yl-4-oxo-butyric acidHCID 58619493(S)-3-Acetoxy-4-morpholin-4-yl-4-oxo-butyric acid

Product 1

HCID 58619497(S)-3-Hydroxy-4-morpholin-4-yl-4-oxo-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (S)-3-Acetoxy-4-morpholin-4-yl-4-oxo-butyric acid and 2-Acetoxy-4-morpholin-4-yl-4-oxo-butyric acid (11 g, 44.8 mmol) in dry methanol (30 mL) HCl in dioxane (4M, 7.3 ml, 29.16 mmol) was added and stirred at room temperature for 5 hrs. The reaction mixture was neutralized with solid NaHCO3, filtered through a mixture of Celite/Na2SO4 (1:1) and concentrated under reduced pressure. Column chromatography on silica eluting with a mixture of ethyl acetate and methylene chloride gave (S)-3-Hydroxy-4-morpholin-4-yl-4-oxo-butyric acid methyl ester (6 g).

Workup

  1. additionwas added
  2. filtrationfiltered through a mixture of Celite/Na2SO4 (1:1)
  3. concentrationconcentrated under reduced pressure
  4. additionColumn chromatography on silica eluting with a mixture of ethyl acetate and methylene chloride

Sources & evidence

ORD record
ord-85bb7806e90448aba9e1ebbf343ae9ee
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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