Dimethylformamide → HCID 58237942, compound

HRID 1192932Notes

Reaction equation

HRID 1192932 reaction equation
[CH2:1]([C@:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH3:11])[C:6](=[O:19])[CH2:5]1)[CH:2]=[CH2:3].CN(C=[O:30])C>Cl[Pd]Cl.Cl[Cu]>[Br:18][C:15]1[CH:14]=[CH:13][C:12]([C@@H:10]([N:7]2[CH2:8][CH2:9][C@:4]([CH2:1][C:2](=[O:30])[CH3:3])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:5][C:6]2=[O:19])[CH3:11])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 44194570HCID 44194570, compound

Product 1

HCID 58237942HCID 58237942, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalyst

Procedure

In a three-necked flask, a mixture of PdCl2 (180 mg, 1 mmol) and CuCl (500 mg, 5 mmol) in aqueous DMF (15 mL of DMF and 5 mL of water) was stirred under an oxygen atmosphere for 1 h at rt, and (S)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-phenylpiperidin-2-one (2 g, purity=65%, 3.3 mmol) was added. The mixture was stirred vigorously under an oxygen atmosphere for 24 h at rt. The reaction mixture was quenched with aq NaHCO3 solution. The organic phase was washed with brine, and dried over NaSO4. After evaporation of the solvent, the residue was purified by prep TLC to give (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-oxopropyl)-4-phenylpiperidin-2-one (400 mg, 29.6%))

Workup

  1. stirringThe mixture was stirred vigorously under an oxygen atmosphere for 24 h at rt
  2. customThe reaction mixture was quenched with aq NaHCO3 solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over NaSO4
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by prep TLC

Sources & evidence

ORD record
ord-946d7e173e13448da0d3c2067ceb3f98
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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