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

HRID 730165

反応式

HRID 730165 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e3f8471f3bc24864ab0a6bc60f92aeb9
出典データセット
uspto-grants-2009_09
特許番号
US07582666B2

関連ノート

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