HCID 21055322, compound → HCID 21055323, compound

HRID 2215269Notes

Reaction equation

HRID 2215269 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@@H:12]([CH2:22][CH3:23])[CH2:13][O:14]CC2C=CC=CC=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1>[OH-].[Pd+2].[OH-].C(O)C>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7]([O:10][CH2:11][C@@H:12]([CH2:22][CH3:23])[CH2:13][OH:14])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 21055322HCID 21055322, compound

Product 1

HCID 21055323HCID 21055323, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

1.5 g (0.0043 mol) of 2-(S)-ethyl-3-benzyloxypropyl p-toluenesulfonate (XVIIId-1), 12 ml of ethanol and 0.29 g of 20% palladium hydroxide are introduced into a 100 ml round-bottomed flask. The mixture is vigorously stirred at ambient temperature under a slight hydrogen pressure. After reacting for one hour, the mixture is filtered through celite and the solid is washed with ethanol. The filtrate is concentrated under reduced pressure and the residue is purified by flash chromatography on silica gel (eluent: dichloromethane/cyclohexane=80:20). 1.02 g (0.0039 mol) of the title compound (XIXd-1) are recovered in the form of a colorless oil.

Workup

  1. filtrationthe mixture is filtered through celite
  2. washthe solid is washed with ethanol
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/cyclohexane=80:20)

Sources & evidence

ORD record
ord-97114eff8f3b48e393819b4823cb6cbd
Source dataset
uspto-grants-2006_09
Patent number
US07109234B2

Reaction notes

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