HCID 22874373, compound → HCID 10881726, compound

HRID 263442Notes

Reaction equation

HRID 263442 reaction equation
C([O:8][C:9]([C@H:11]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:12][C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:19])[Cl:18])=[O:14])=[O:10])C1C=CC=CC=1>CO.[Pd]>[Cl:18][C:17]([Cl:19])([Cl:20])[CH2:16][O:15][C:13]([CH2:12][C@@H:11]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:9]([OH:10])=[O:8])=[O:14]

Participants

4

Reactant 1

HCID 22874373HCID 22874373, compound

Product 1

HCID 10881726HCID 10881726, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,2,2-Trichloroethyl 3-(R)-benzyloxycarbonyloctanoate (924 mg), prepared in Referential Example 8, was dissolved in methanol (8 ml) and was catalytically reduced by stirring the solution for 2 hours under an atmosphere of hydrogen in the presence of 10% palladium on charcoal (52 mg). After completion of the reaction, the catalyst was removed by celite filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography through silica gel using a 30:1 mixture of chloroform and methanol as an eluent, to give the desired compound (678 mg) as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed by celite filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel using
  5. additiona 30:1 mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-753802ae07c04c4f9f98a6cef065046b
Source dataset
uspto-grants-1997_07
Patent number
US05643908

Reaction notes

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