Phthalimide → Tert-Butyl 1-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]cyclopropanecarboxylate

HRID 238161노트

반응식

HRID 238161 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:21]=[C:19]1[C:18]2[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](=[O:26])[N:20]1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1

참가 물질

5

반응물 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 21932036Tert-Butyl 1-(4-bromobutyl)cyclopropanecarboxylate

생성물 1

HCID 58074557Tert-Butyl 1-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]cyclopropanecarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

Under argon, 4.2 g (15.15 mmol) of tert-butyl 1-(4-bromobutyl)cyclopropanecarboxylate were initially charged in 50 ml of DMF, 3.34 g (22.72 mmol) of phthalimide and 4.19 g (30.3 mmol) of potassium carbonate were added and the mixture was stirred at 90° C. for 2 h. The reaction mixture was then filtered, and the filtrate was diluted with water and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. The product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 4.23 g (81.3% of theory) of the target compound.

후처리

  1. filtrationThe reaction mixture was then filtered
  2. additionthe filtrate was diluted with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

출처 및 근거

ORD 기록
ord-707a1d3449964e54845d2cbc9dfc88a7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642592B2

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