Propargyl bromide → (3S)-3-ethoxycarbonyl-4-(2-propynyl)morpholine

HRID 584234Notes

Reaction equation

HRID 584234 reaction equation
Cl.[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][O:11][CH2:10][CH2:9][NH:8]1)=[O:6])[CH3:3].[CH2:13](Br)[C:14]#[CH:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][O:11][CH2:10][CH2:9][N:8]1[CH2:15][C:14]#[CH:13])=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 44828818Ethyl (3S)-morpholine-3-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 57078218(3S)-3-ethoxycarbonyl-4-(2-propynyl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3S)-3-ethoxycarbonylmorpholine hydrochloride (0.3 g), propargyl bromide (0.34 ml) and potassium carbonate (0.91 g) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 1 hour and then the solvent was removed under reduced pressure. Ethyl acetate and sodium hydrogen carbonate solution were added to the residue and the organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (3:7) as an eluent to give (3S)-3-ethoxycarbonyl-4-(2-propynyl)morpholine (0.22 g) as an oil.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionEthyl acetate and sodium hydrogen carbonate solution were added to the residue
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (3:7) as an eluent

Sources & evidence

ORD record
ord-c0f1f937bea2408497270dfb01a73caf
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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