Benzaldehyde → (R)-4-Hydroxy-5-methyl-3-[(3-methyl-1H-indol-2-yl)-phenyl-methyl]-5-phenyl-1,5-dihydro-pyrrol-2-one

HRID 1432502Notes

Reaction equation

[OH:1][C:2]1[C@@:6]([CH3:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:4](=[O:14])[CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1>>[OH:1][C:2]1[C@@:6]([CH3:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:4](=[O:14])[C:3]=1[CH:15]([C:25]1[NH:26][C:27]2[C:32]([C:24]=1[CH3:23])=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 6736Skatole

HCID 69071890(R)-4-hydroxy-5-methyl-5-phenyl-1,5-dihydro-pyrrol-2-one

Product 1

HCID 57933473(R)-4-Hydroxy-5-methyl-3-[(3-methyl-1H-indol-2-yl)-phenyl-methyl]-5-phenyl-1,5-dihydro-pyrrol-2-one

Procedure

Using general procedure D, (R)-4-hydroxy-5-methyl-5-phenyl-1,5-dihydro-pyrrol-2-one (prepared according to Lit. 11, see also Lit. 19) was reacted with benzaldehyde and 3-methyl-1H-indole to give the title compound as a yellow foam. MS: 409.2 ([M+H]+).

Workup

customprepared

Sources & evidence

ORD record: ord-f3a41c59fda74680a6010a435d1b7497
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

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