Trifluoroacetic acid → 1-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidine

HRID 634033노트

반응식

HRID 634033 반응식
[CH:1]([N:14]1[CH2:17][C:16]([C:19]2[O:20][C:21]3[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=3[C:23]=2[CH3:24])(O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.B(F)(F)F.CCOCC>ClCCl>[CH:1]([N:14]1[CH2:17][CH:16]([C:19]2[O:20][C:21]3[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=3[C:23]=2[CH3:24])[CH2:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 671545491-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidin-3-ol

생성물 1

HCID 671546541-Benzhydryl-3-(3-methylbenzofuran-2-yl)azetidine수율 63%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled (0° C.) solution of 1-benzhydryl-3-(3-methylbenzofuran-2-yl)azetidin-3-ol (406 mg, 1.099 mmol) in dichloromethane (50 mL) were added triethylsilane (1.775 mL, 10.99 mmol) and trifluoroacetic acid (1.630 mL, 22.01 mmol). The reaction mixture was warmed to rt and stirred for 23 h. After 18 h, boron trifluoride etherate (0.6 mL, 4.73 mmol) was added and the reaction was allowed to stir for an additional 5 h. The reaction mixture was partitioned between sat. NaHCO3 and DCM. The layers were separated, the organic layer was washed with sat. NaHCO3 and brine, dried on Na2SO4 and concentrated. The residue was purified by flash chromatography (heptane/EtOAc, 0%->30%), yielding the title product (244 mg, 63%) as an off-white solid.

후처리

  1. waitAfter 18 h
  2. stirringto stir for an additional 5 h
  3. customThe reaction mixture was partitioned between sat. NaHCO3 and DCM
  4. customThe layers were separated
  5. washthe organic layer was washed with sat. NaHCO3 and brine
  6. customdried on Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (heptane/EtOAc, 0%->30%)

출처 및 근거

ORD 기록
ord-af1945a8be5f44ce8f5a3a99b42e7992
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321769B2

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