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

HRID 1796943

반응식

HRID 1796943 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3fb4dbecaf0849ebb432e18ac9688504
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034017B2

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