Arcyriarubin A → 3,4-bis(1H-indol-3-yl)-2,5-dihydro-1H-pyrrol-2-one

HRID 345663

반응식

HRID 345663 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:17](=[O:31])[NH:18][C:19](=O)[C:20]=2[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)=[CH:8]1>C(OCC)C.C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[C:17](=[O:31])[NH:18][CH2:19][C:20]=2[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)=[CH:8]1

참가 물질

5

반응물 2

HCID 2399Arcyriarubin AHCID 21226445Aluminium lithium hydride

생성물 1

HCID 53276503,4-bis(1H-indol-3-yl)-2,5-dihydro-1H-pyrrol-2-one수율 18.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

20 ml of a 1M solution of LiAlH4 in diethyl ether was added to a solution of 1.0 g of 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione in 140 ml of THF. The mixture was stirred for 18 hours under nitrogen. The mixture was cooled to 0° C., quenched with 50 ml of water, then acidified to pH 2 with 2M hydrochloric acid and extracted with ethyl acetate. The organic extracts were washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was purified on silica gel with 5-10% methanol in dichloromethane. The first product eluted was triturated with ethyl acetate/hexane to give 175 mg of 3,4-bis(3-indolyl)-3-pyrrolin-2-one, m.p. 290°-293° C. (decomposition). The second product eluted was crystallized from ethyl acetate/chloroform to give 490 mg of 5-hydroxy-3,4-bis(3-indolyl)-3-pyrrolin-2-one, m.p. above 250° C. (decomposition).

후처리

  1. customquenched with 50 ml of water
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with saturated sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. customThe residue was purified on silica gel with 5-10% methanol in dichloromethane
  7. washThe first product eluted
  8. customwas triturated with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-4f5b573773694b3ca8ac6ab6160a6328
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057614

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