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

HRID 83082ノート

反応式

HRID 83082 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-944120d9480b472890df3b5b4b9e85b6
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

反応ノート

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