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

HRID 1432503Notes

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]=[C:30]([CH3:33])[CH:31]=2)[NH:26][CH:25]=1>>[CH3:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([CH3:33])[CH:31]=2)[NH:26][C:25]=1[CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[C:4](=[O:14])[NH:5][C@:6]([CH3:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]=1[OH:1]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 986153,5-Dimethylindole

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

Product 1

HCID 57933441(R)-3-[(3,5-Dimethyl-1H-indol-2-yl)-phenyl-methyl]-4-hydroxy-5-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 3,5-dimethyl-1H-indole (Lit. 21) to give the title compound as a yellow foam. MS: 423.3 ([M+H]+).

Workup

customprepared

Sources & evidence

ORD record: ord-d0b569313487446d813e15f877e43a32
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612099B2

Reaction notes

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