HCID 23564196, compound → HCID 18670159, compound

HRID 1059320Notes

Reaction equation

HRID 1059320 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]=[O:25])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])(O)(O)=[O:27].[Na+].Cl([O-])=O.[Na+]>O.CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:27])=[O:25])=[CH:19][CH:18]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 23564196HCID 23564196, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 18670159HCID 18670159, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×

Procedure

To a solution of 0.7 g of 4-[1-(benzyloxycarbonyl)-piperidin-4-yl]phenylacetaldehyde and 0.5 g of sodium dihydrogenphosphate in 5 ml of water and 30 ml of dimethyl sulfoxide was added a solution of 0.35 g of sodium chlorite in water (5 ml) and the resulting mixture was reacted at room temperature for 20 minutes. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 0.7 g of the title compound was obtained as a colorless oily substance.

Workup

  1. customthe resulting mixture was reacted at room temperature for 20 minutes
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-eac98194f0ac4ab19a9fd17dfa6e4103
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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