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

HRID 1173600Notes

Reaction equation

HRID 1173600 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([CH3:14])[NH:12][C:11](=[O:15])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>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]>[Si:1]([O:8][C@H:9]1[CH2:10][C:11](=[O:15])[N:12]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:26])([F:28])[F:27])[CH:18]=2)[C@H:13]1[CH3:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

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 59556992HCID 59556992, compound

Product 1

HCID 595569734-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one (5.00 g), 4-iodo-2-(trifluoromethyl)benzonitrile (6.80 g), cesium carbonate (10.65 g), tris(dibenzylideneacetone)dipalladium(0) (1.00 g) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (2.52 g), and in the same manner as in Reference Example 3, the title compound was obtained as a colorless solid (yield: 5.617 g, yield: 64.7%).

Sources & evidence

ORD record
ord-583536fb4251430aadad26aadd9df2bd
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

Loading…