N,N-Dimethylaniline → (5S)-5-(Aminomethyl)-3-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1,3-oxazolidin-2-one

HRID 730165

Reaction equation

HRID 730165 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1C=CC=CC=1)=[O:3].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])=[CH:15][CH:14]=1.[CH3:25][N:26](C)C1C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[NH2:26][CH2:25][C@@H:5]1[O:4][C:2](=[O:3])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[CH:15][CH:14]=2)[CH2:6]1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 676146Pyrrolidinone, (4-aminophenyl)-

Product 1

HCID 11666268(5S)-5-(Aminomethyl)-3-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

At −20° C., benzyl chloroformate (4.27 g, 25.03 mmol) is slowly added dropwise to 1-(4-aminophenyl)pyrrolidin-2-one (4 g, 22.7 mmol) and N,N-dimethylaniline (3.6 ml, 28.4 mmol) in tetrahydrofuran (107 ml). The reaction mixture is stirred at −20° C. for 30 min and then warmed to room temperature. After addition of ethyl acetate (0.5 l), the organic phase is washed with saturated NaCl solution (0.5 l). The combined organic phase are dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residue is titrated with diethyl ether and filtered off with suction. Yield: 5.2 g, 74% of theory, light-beige crystals, melting point: 174° C.

Workup

  1. temperaturewarmed to room temperature
  2. washthe organic phase is washed with saturated NaCl solution (0.5 l)
  3. dry with materialThe combined organic phase are dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-e3f8471f3bc24864ab0a6bc60f92aeb9
Source dataset
uspto-grants-2009_09
Patent number
US07582666B2

Linked notes

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