Sodium Carbonate → 1-[3-Methoxy-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol

HRID 2198052

반응식

HRID 2198052 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].Br[CH2:15][CH:16]([OH:20])[CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:6]2[CH2:18][CH2:17][CH:16]([OH:20])[CH2:15]2)[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

참가 물질

4

반응물 3

HCID 10340Sodium CarbonateHCID 295701,4-Dibromo-2-butanolHCID 6056715-(Trifluoromethyl)-m-anisidine

생성물 1

HCID 670222831-[3-Methoxy-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol수율 47%

실험 절차

3-Methoxy-5-(trifluoromethyl)aniline (15.0 g) and 1,4-dibromobutan-2-ol (18.3 g) were stirred at 100° C. for 3 hr. After cooling to room temperature, to the reaction mixture was added saturated aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-50:50) to give the title compound (9.57 g, yield 47%) as an orange oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-50:50)

출처 및 근거

ORD 기록
ord-3ccd6a71f3a2457f9a639a45b543f266
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338622B2

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