Phthalimide → (5)-2-(1-(4-(Methoxy)phenyl)ethyl)isoindoline-1,3-dione

HRID 709434

반응식

HRID 709434 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.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20](N)[CH3:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CCCCO>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]([N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH3:21])=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 793467(S)-1-(4-Methoxyphenyl)ethylamine

생성물 1

HCID 101694173(5)-2-(1-(4-(Methoxy)phenyl)ethyl)isoindoline-1,3-dione수율 64.6%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
160 °C

실험 절차

To phthalimide (1.3 g, 0.0088 mol) in a 2-5 mL microwave vial was added (S)-1-(4-methoxyphenyl)ethan-1-amine (2.20 mL, 0.015 mol) and K2CO3 (1.2 g, 0.0087 mol). The reaction mixture capped and heated at 160° C. for 2 minutes. The resulting crude solid was suspended in n-BuOH and was filtered. The filtrate was put aside. The solid was washed with H2O and the filtrate was discarded. The solid was washed with CH2Cl2 and the resulting filtrate was partitioned with H2O. The organics (n-BuOH and CH2Cl2 layer) were combined and concentrated. The crude residue was purified by silica gel column chromatography using CH2Cl2 as eluent to yield 1.6 g (64%) of the title compound. LC/MS: m/z (ES+) 282 (M+H)+.

후처리

  1. customThe reaction mixture capped
  2. filtrationwas filtered
  3. washThe solid was washed with H2O
  4. washThe solid was washed with CH2Cl2
  5. customthe resulting filtrate was partitioned with H2O
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-c18f34cedcee43ec9062a99d9d271c44
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181200B2

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