Triethylamine → AG-E-14754

HRID 539059

Reaction equation

HRID 539059 reaction equation
Cl[C:2](Cl)([O:4][C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C@@H:14]([CH2:17][CH2:18][CH3:19])CO.CCN(CC)CC>C1COCC1>[CH2:17]([C@H:14]1[CH2:2][O:4][C:5](=[O:11])[NH:13]1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 6951248(2S)-2-aminopentan-1-ol

Product 1

HCID 8063309AG-E-14754Yield 185.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphosgene (0.431 g, 1.45 mmol) in THF (5 mL) was added dropwise to a stirred solution of (S)-2-aminopentan-1-ol (0.500 g, 4.85 mmol) and Et3N (1.49 mL, 10.7 mmol) in THF (22 mL) at 0° C. under N2. The reaction mixture was stirred at ambient temperature for 2 hours. After cooling, the suspension was filtered through GF/F paper and concentrated in vacuo. The residue was taken up in EtOAc and washed with 10% HCl, dried and concentrated to give (S)-4-propyloxazolidin-2-one (0.348 g, 55%) as a clear oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension was filtered through GF/F paper
  3. concentrationconcentrated in vacuo
  4. washwashed with 10% HCl
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cbb784382e724a8da7cfa259d933cd2a
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Linked notes

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