Lithium diisopropylamide → 1,3-Dioxo-2-(2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline

HRID 618694노트

반응식

HRID 618694 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[N:14](C(OC(C)(C)C)=O)[C:13]1=[O:26].C([N-]C(C)C)(C)C.[Li+].Cl([F:39])(=O)(=O)=O>O1CCCC1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1([F:39])[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:26]

참가 물질

4

반응물 2

HCID 2724682Lithium diisopropylamideHCID 15408802Tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidine-1-carboxylate

생성물 1

HCID 98820501,3-Dioxo-2-(2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 1,3-dioxo-2-(1-tert.-butoxycarbonyl-2,6-dioxopiperidin-3-yl)isoindoline (1.0 g. 2.8 mmol) in tetrahydrofuran (10 mL) is added lithium diisopropylamide (1.5 mL, 3.0 mmol, 2 M) at. After 30 minutes, perchloryl fluoride (5 mmol) is bubbled into the mixture. The mixture is allowed to reach room temperature and the solvent then removed in vacuo. The residue is stirred with ethyl acetate (10 mL) and 1N hydrochloric acid (10 mL) for one hour. The organic layer is separated and the solvent removed in vacuo to yield 1,3-dioxo-2-(2,6-dioxo-3-fluoropiperidin-3-yl)isoindoline which can be further purified through chromatography.

후처리

  1. customto reach room temperature
  2. customthe solvent then removed in vacuo
  3. customThe organic layer is separated
  4. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-eb32bc8cf32e4b10ab1ea3d845a98ae6
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955476

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