Cesium carbonate → Rac-4-((4r,5s)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl)-2-chloro-3-methylbenzonitrile

HRID 1967266Notes

Reaction equation

HRID 1967266 reaction equation
[Si:1]([O:8][CH:9]1[CH:13]([CH3:14])[NH:12][C:11](=[O:15])[C:10]1([CH3:17])[CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:18][C:19]1[C:26]([CH3:27])=[C:25](I)[CH:24]=[CH:23][C:20]=1[C:21]#[N:22].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[C@H:13]([CH3:14])[N:12]([C:25]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([Cl:18])[C:26]=2[CH3:27])[C:11](=[O:15])[C:10]1([CH3:16])[CH3:17])([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 167319952-Chloro-4-iodo-3-methylbenzonitrileHCID 67105615(4RS,5RS)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one

Product 1

HCID 59556867Rac-4-((4r,5s)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl)-2-chloro-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using (4RS,5SR)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one (200 mg), 2-chloro-4-iodo-3-methylbenzonitrile (250 mg), cesium carbonate (380 mg), tris(dibenzylideneacetone)dipalladium(0) (36 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (45 mg), and in the same manner as in Reference Example 3, the title compound was obtained as a pale-yellow oil (yield: 103 mg, yield: 33.7%).

Sources & evidence

ORD record
ord-813732f229ac41a7bb466a83f81265b0
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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