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

HRID 1504070

반응식

HRID 1504070 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a2e299f1e8e84a29b2dd541793573257
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212190B2

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