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

HRID 709434

反応式

HRID 709434 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
160 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c18f34cedcee43ec9062a99d9d271c44
出典データセット
uspto-grants-2015_11
特許番号
US09181200B2

関連ノート

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