Cesium carbonate → 4-[(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxopyrrolidin-1-yl]-2-methoxybenzonitrile

HRID 1967392Notes

Reaction equation

HRID 1967392 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[OH:12][C@:13]1([CH3:20])[C@H:17]([CH3:18])[NH:16][C:15](=[O:19])[CH2:14]1.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]>[OH:12][C@@:13]1([CH3:20])[CH2:14][C:15](=[O:19])[N:16]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=2)[C@H:17]1[CH3:18]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 223467024-Bromo-2-methoxybenzonitrileHCID 55299894(4S,5S)-4-hydroxy-4,5-dimethylpyrrolidin-2-one

Product 1

HCID 595568664-[(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxopyrrolidin-1-yl]-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using 4-bromo-2-methoxybenzonitrile (684 mg), (4S,5S)-4-hydroxy-4,5-dimethylpyrrolidin-2-one (500 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (286 mg), tris(dibenzylideneacetone)dipalladium(0) (148 mg) and cesium carbonate (1.55 g), and in the same manner as in Example 62, the title compound was obtained as a colorless amorphous solid (yield: 410 mg, 48%).

Sources & evidence

ORD record
ord-34c8a06133594cc6a0c875c52aa41ac6
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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