Acetic Acid → HCID 15117293, compound

HRID 1029658Notes

Reaction equation

HRID 1029658 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][C@H:8]1[C:13]([CH:15]1C(=O)OC(C)(C)OC1=O)=[O:14])=[O:6])[CH:2]=[CH2:3].C(O)(=O)C>O>[C:13]([C@@H:8]1[CH2:9][O:10][CH2:11][CH2:12][N:7]1[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])(=[O:14])[CH3:15]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 15117292HCID 15117292, compound

Product 1

HCID 15117293HCID 15117293, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-[(3S)-4-allyloxycarbonylmorpholin-3-yl]carbonyl-2,2-dimethyl-1,3-dioxane-4,6-dione (8.30 g) in a mixture of glacial acetic acid (17 ml) and water (25 ml) was refluxed for 2 hours. After cooling, the mixture was concentrated under reduced pressure to give a syrup. A solution of the syrup in ethyl acetate (100 ml) was washed in turn with water (100 ml), saturated sodium hydrogen carbonate (100 ml), and brine (100 ml). The solution was dried over magnesium sulfate and evaporated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (40 g) and eluted with a mixture of hexane and ethyl acetate (8:2, V/V) to give (3S)-3-acetyl-4-allyloxycarbonylmorpholine (3.7 g) as a syrup.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customto give a syrup
  5. washA solution of the syrup in ethyl acetate (100 ml) was washed in turn with water (100 ml), saturated sodium hydrogen carbonate (100 ml), and brine (100 ml)
  6. dry with materialThe solution was dried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto give a syrup
  9. washeluted with a mixture of hexane and ethyl acetate (8:2, V/V)

Sources & evidence

ORD record
ord-a32fb3bc8b464c83b7b443a5eb5bc9fb
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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