cis-1,2,3,6-Tetrahydrophthalimide → (3aR,7aS)-rel-2,3,3a,4,7,7a-Hexahydro-1H-isoindole

HRID 720468

반응식

HRID 720468 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(=O)[NH:11][C:10](=O)[C@H:9]2[CH2:13][CH:14]=[CH:15][CH2:16][C@@H:8]12>C1COCC1>[CH2:10]1[C@@H:9]2[C@@H:8]([CH2:16][CH:15]=[CH:14][CH2:13]2)[CH2:7][NH:11]1

참가 물질

4

반응물 2

HCID 92888cis-1,2,3,6-TetrahydrophthalimideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 16765331(3aR,7aS)-rel-2,3,3a,4,7,7a-Hexahydro-1H-isoindole수율 86.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

A suspension of lithium aluminum hydride (21.4 g, 0.562 mol) in THF (700 mL) at room temperature was treated with cis-1,2,3,6-tetrahydrophthalimide (Aldrich; 37 g, 0.245 mol) in small portions. The reaction mixture was stirred at 60° C. overnight then cooled to room temperature and quenched carefully by the sequential addition of water (22 mL), THF (22 mL), 15% aqueous KOH (22 mL), and water (80 mL). The mixture was diluted with diethyl ether (100 mL), stirred at room temperature for 1 hour, and then filtered (methylene chloride wash). The filtrate was concentrated under reduced pressure to provide the title compound as an oil (26.1 g). 1H NMR (CDCl3, 300 MHz) δ 1.76–2.02 (m, 2H), 2.10–2.33 (m, 3H), 2.34–2.56 (m, 2H), 2.61–2.79 (m, 2H), 2.87–3.17 (m, 2H), 5.53–6.03 (m, 2H); MS (DCI/NH3) m/z 124 (M+H)+.

후처리

  1. temperaturethen cooled to room temperature
  2. customquenched carefully by the sequential addition of water (22 mL), THF (22 mL), 15% aqueous KOH (22 mL), and water (80 mL)
  3. additionThe mixture was diluted with diethyl ether (100 mL)
  4. stirringstirred at room temperature for 1 hour
  5. filtrationfiltered
  6. wash(methylene chloride wash)
  7. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2ba0ec14a5b3474b830853cd83ec00dd
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135484B2

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