Acetonitrile → 1-Benzhydryl-3-(4-fluorophenoxy)azetidine

HRID 72400

반응식

HRID 72400 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(#N)C.CS(O[CH:17]1[CH2:20][N:19]([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18]1)(=O)=O>>[CH:21]([N:19]1[CH2:20][CH:17]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:18]1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

4

반응물 3

HCID 6342AcetonitrileHCID 97324-FluorophenolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

생성물 1

HCID 150533691-Benzhydryl-3-(4-fluorophenoxy)azetidine

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 4-fluorophenol (0.80 g, 7.16 mmol) in acetonitrile (15 ml) potassium carbonate (1.3 g, 9.30 mmol) was added followed by the addition of 1-benzhydrylazetidin-3-yl methanesulfonate (D19) (2.5 g, 7.87 mmol) and the mixture was stirred under microwave irradiation at 100° C. for 5 mins. The reaction mixture was evaporated in vacuo and the residue was taken up in a mixture diethylether/water (10 ml/10 ml). The aqueous layer was extracted with diethylether (2×10 ml). The organics after solvent evaporation were loaded on SPE-Si (25 g) cartridge eluting with a mixture cyclohexane/ethylacetate (from 100/0 to 85/15. Collected fractions gave, after evaporation, the title compound (D21) (1.8 g).

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. extractionThe aqueous layer was extracted with diethylether (2×10 ml)
  3. customThe organics after solvent evaporation
  4. washeluting with a mixture cyclohexane/ethylacetate (from 100/0 to 85/15
  5. customCollected fractions gave
  6. customafter evaporation

출처 및 근거

ORD 기록
ord-028f9f14d71c423cb695e1e1704bf127
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828987B2

연결된 노트

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