Trifluoroacetic acid → 4-fluoro-2,3-dihydro-1H-isoindol-1-one

HRID 877234노트

반응식

HRID 877234 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4](O)[NH:5][C:6]2=[O:11].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 668996124-fluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

생성물 1

HCID 220646804-fluoro-2,3-dihydro-1H-isoindol-1-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4.05 g (about 24.2 mmol) of 4-fluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one were initially charged in 10 ml of dichloromethane, 22.4 ml (290.8 mmol) of trifluoroacetic acid and 7.7 ml (48.5 mmol) of triethylsilane were added and the mixture was stirred at RT overnight. The reaction mixture was then concentrated and the residue was dissolved in dichloromethane and washed with sodium bicarbonate solution. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1 to 1:1). This gave 890 mg (24.2% of theory) of the target compound.

후처리

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with sodium bicarbonate solution
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1 to 1:1)

출처 및 근거

ORD 기록
ord-c14164ba6d434abdb9d050b4df5652f5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987256B2

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