tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate → tert-Butyl cyclopentyl{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate

HRID 877223노트

반응식

HRID 877223 반응식
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=1>CN(C=O)C>[CH:29]1([CH:21]([C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:5]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])=[CH:16][CH:17]=2)[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:33][CH2:32][CH2:31][CH2:30]1

참가 물질

4

반응물 2

HCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetateHCID 24194345Phthalimide potassium salt2회

생성물 1

HCID 58136372tert-Butyl cyclopentyl{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Under argon, 6.49 g (35 mmol) of potassium phthalimide were initially charged in 60 ml of DMF, 15 g (31.8 mmol) of tert-butyl(+/−)-2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate were added and the mixture was stirred at 80° C. overnight. A further 0.5 equivalent of potassium phthalimide was then added, and the mixture was stirred at 80° C. for another 6 h. The reaction mixture was then filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with ethanol and the solid was filtered off with suction, washed with ethanol and dried under high vacuum. This gave 8.5 g (about 96% pure, 61% of theory) of the target compound.

후처리

  1. stirringthe mixture was stirred at 80° C. for another 6 h
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was triturated with ethanol
  5. filtrationthe solid was filtered off with suction
  6. washwashed with ethanol
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-a607e56ac90f428fbb4cc64d3a909d68
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987256B2

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