Triethylamine → (S)-METHYL MORPHOLINE-3-CARBOXYLATE

HRID 1437276Notes

Reaction equation

HRID 1437276 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:18])[C@@H:11]([NH2:17])[CH2:12][O:13][CH2:14][CH2:15]Cl>CO>[CH3:8][O:9][C:10]([C@@H:11]1[CH2:12][O:13][CH2:14][CH2:15][NH:17]1)=[O:18]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86605437HCID 86605437, compound

Product 1

HCID 6558896(S)-METHYL MORPHOLINE-3-CARBOXYLATE

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (1.2 mL) was added to the above-obtained (2S)-2-amino-3-(2-chloroethoxy)propanoic acid methyl ester (726 mg) in methanol (10 mL), and the resultant mixture was refluxed under heat for 3 hours, and then cooled in air. The reaction solvent was removed under reduced pressure. Ethyl acetate was added to the residue, and insoluble matter was removed by filtration. The solvent of the filtrate was removed under reduced pressure, to thereby give the title compound as an oily product (467 mg, 80%).

Workup

  1. temperatureunder heat for 3 hours
  2. temperaturecooled in air
  3. customThe reaction solvent was removed under reduced pressure
  4. additionEthyl acetate was added to the residue, and insoluble matter
  5. customwas removed by filtration
  6. customThe solvent of the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-1e69003d772f40dcaa0000907fd03886
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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