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

HRID 345663

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-4f5b573773694b3ca8ac6ab6160a6328
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05057614

Linked notes

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