HCID 18624159, compound → HCID 18624193, compound

HRID 1860630Notes

Reaction equation

HRID 1860630 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[C:16]([CH3:23])([CH3:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.P(=O)(O)(O)O.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([CH3:23])([CH3:22])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 18624159HCID 18624159, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18624193HCID 18624193, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 1004Phosphoric AcidSolvent

Procedure

A solution of the product of STEP 3 in methanol and phosphoric acid (catalytic amount) was shaken in Parr hydrogenation apparatus with 20% Pd(OH)2/C under 60 psi hydrogen pressure for 9 hours. The solution was filtered and filtrate concentrated in vacuo. An ether solution of the residue was treated with excess diazomethane in ether at 0° C. The resulting solution was concentrated in vacuo and the residue was purified by chromatography over silica gel using 10% ethyl acetate in hexane as eluant to provide the above compound as a colorless thick liquid.

Workup

  1. filtrationThe solution was filtered
  2. concentrationfiltrate concentrated in vacuo
  3. additionAn ether solution of the residue was treated with excess diazomethane in ether at 0° C
  4. concentrationThe resulting solution was concentrated in vacuo
  5. customthe residue was purified by chromatography over silica gel using 10% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-c848c8d47a994256b2355a2671672910
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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