4-Amino-1-butanol → 2-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dione

HRID 1504070

反応式

HRID 1504070 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])N1C(OCC)=O>C1COCC1>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][N:1]1[C:8](=[O:7])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17]

参加物

4

反応物 2

HCID 258684-Amino-1-butanolHCID 31187N-Carbethoxyphthalimide

生成物 1

HCID 111175282-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dione収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-aminobutan-1-ol (18 g, 201.94 mmol, 1.00 equiv), ethyl 1,3-dioxo-2,3-dihydro-1H-isoindole-2-carboxylate (44.5 g, 203.02 mmol, 1.01 equiv) and TEA (28 g, 276.71 mmol, 1.37 equiv) in 500 mL of THF was heated to reflux overnight. The reaction mixture was cooled to room temperature, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with PE/EtOAc (10:1 to 1:1) to give 30 g (68%) of 2-(4-hydroxybutyl)-2,3-dihydro-1H-isoindole-1,3-dione as a white solid. MS (ES): m/z 220 (M+H)+.

後処理

  1. temperatureto reflux overnight
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solids were filtered out
  7. concentrationthe filtrate was concentrated under vacuum

出典と根拠

ORDレコード
ord-a2e299f1e8e84a29b2dd541793573257
出典データセット
uspto-grants-2015_12
特許番号
US09212190B2

関連ノート

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