Benzoic Acid → 4-(3,4,5-Trifluorophenyl)aminotetrahydropyran

HRID 561179노트

반응식

HRID 561179 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:10])[C:8]=1[F:9])[NH2:5].[O:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O)(=O)C1C=CC=CC=1.[Na].[BH4-].[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][CH:14]2[CH2:15][CH2:16][O:11][CH2:12][CH2:13]2)[CH:6]=[C:7]([F:10])[C:8]=1[F:9]

참가 물질

5

반응물 4

HCID 243Benzoic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 27249913,4,5-TrifluoroanilineHCID 131729286sodium NaBH4

생성물 1

HCID 590029984-(3,4,5-Trifluorophenyl)aminotetrahydropyran수율 41.4%

실험 절차

To a mixture of 3,4,5-trifluoroaniline (3.70 g, 25.1 mmol), tetrahydro-4H-pyran-4-one (2.52 g, 25.1 mmol), and benzoic acid (3.07 g, 25.1 mmol), was added sodium NaBH4 (0.95 g, 25.1 mmol), the whole mixture was stirred at room temperature for 1.5 h. After quenching with the reaction mixture with 1 M aq. NaOH under cooling with ice, the whole mixture was extracted with Et2O. The extract was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography of the residue (hexane:EtOAc=3:2) gave 4-(3,4,5-trifluorophenyl)aminotetrahydropyran (2.40 g, 41%) as a white powder.

후처리

  1. customAfter quenching with the reaction mixture with 1 M aq. NaOH
  2. temperatureunder cooling with ice
  3. extractionthe whole mixture was extracted with Et2O
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e742700a7c074932902206bbe5236fda
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063221B2

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