Cesium carbonate → 4-[(2S,3S)-2-ethyl-3-hydroxy-3-methyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

HRID 1967396Notes

Reaction equation

HRID 1967396 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH2:14]([C@@H:16]1[NH:20][C:19](=[O:21])[CH2:18][C@@:17]1([OH:23])[CH3:22])[CH3:15].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:14]([C@H:16]1[C@:17]([OH:23])([CH3:22])[CH2:18][C:19](=[O:21])[N:20]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1)[CH3:15]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 162183374-Iodo-2-(trifluoromethyl)benzonitrileHCID 55299895(4S,5S)-5-ethyl-4-hydroxy-4-methylpyrrolidin-2-one

Product 1

HCID 595568934-[(2S,3S)-2-ethyl-3-hydroxy-3-methyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-iodo-2-(trifluoromethyl)benzonitrile (605 mg), (4S,5S)-5-ethyl-4-hydroxy-4-methylpyrrolidin-2-one (350 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (180 mg), tris(dibenzylideneacetone)dipalladium(0) (93 mg) and cesium carbonate (929 mg), and in the same manner as in Example 62, the title compound was obtained as a white powder (yield: 422 mg, 66%).

Sources & evidence

ORD record
ord-f558ab8959de4c288bfcf80264fc1e59
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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