Water → HCID 58237927, compound

HRID 1192929Notes

Reaction equation

HRID 1192929 reaction equation
[CH2:1]([C:4]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[CH2:11][CH3:12])[C:6](=[O:20])[CH2:5]1)[CH:2]=[CH2:3].[OH2:27].O=O>CN(C=O)C.CCOC(C)=O.[Cu]Cl.[Pd](Cl)Cl>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([C@@H:10]([N:7]2[CH2:8][CH2:9][C:4]([CH2:1][C:2](=[O:27])[CH3:3])([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:5][C:6]2=[O:20])[CH2:11][CH3:12])=[CH:18][CH:17]=1

Participants

8

Reactant 3

HCID 962WaterHCID 977OxygenHCID 58237935HCID 58237935, compound

Product 1

HCID 58237927HCID 58237927, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A round-bottom flask was charged with copper(I) chloride (0.3100 g, 3.13 mmol), and a solution of 4-allyl-1-((S)-1-(4-bromophenyl)propyl)-4-phenylpiperidin-2-one (0.3045 g, 0.74 mmol) in DMF (7.5 mL) was added, followed by H2O (2 mL) and palladium(II) chloride (0.0670 g, 0.38 mmol). The reaction mixture was vigorously stirred under a balloon of oxygen for 20 h at rt and diluted with EtOAc, dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford 0.2475 g (78%) of 1-((S)-1-(4-bromophenyl)propyl)-4-(2-oxopropyl)-4-phenylpiperidin-2-one. LC-MS Method 3 tR=1.87, 1.93 min, m/z 428, 430 (MH+).

Workup

  1. dry with materialdried over Na2SO4
  2. customAfter the solvents were evaporated
  3. customthe residue was purified by chromatography on silica gel
  4. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-8949edc4b98b4b98a29812bc506b0b54
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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