Oxygen → HCID 67046465, compound

HRID 1394459Notes

Reaction equation

HRID 1394459 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:15]2[CH:16]=[N:17][N:18](CC3C=CC=CC=3)[CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].O=O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:15]2[CH:16]=[N:17][NH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 977OxygenHCID 23665647Potassium tert-butoxideHCID 67046276HCID 67046276, compound

Product 1

HCID 67046465HCID 67046465, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(1-phenyl-1-(1-benzylpyrazol-4-yl)-methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.079 g, 0.18 mmol) in DMSO (0.2 mL) was added potassium tert-butoxide solution (1 M in THF, 2.0 mL, 2.0 mmol) and O2 was bubbled through the stirring mixture for 15 min. The reaction mixture was then quenched with saturated aqueous NH4Cl (2 mL) and extracted with EtOAc (×2). The combined organic phase was dried (Na2SO4) and evaporated, and the resulting residue was purified by preparative HPLC to give the title compound (0.024 g, 39%) as a gum:

Workup

  1. customwas bubbled through the stirring mixture for 15 min
  2. customThe reaction mixture was then quenched with saturated aqueous NH4Cl (2 mL)
  3. extractionextracted with EtOAc (×2)
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. customevaporated
  6. customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5ee3fd7118294a5493b85c902a4575ee
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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