(+/-)-alpha-(6-(Benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanol → alpha-(6-Hydroxy-2-naphthyloxymethyl)-3-pyridinepropanol

HRID 1600907Notes

Reaction equation

HRID 1600907 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][CH2:20][CH:21]([OH:30])[CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH:13]=[CH:12]2)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][CH2:20][CH:21]([OH:30])[CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH:13]=[CH:12]2

Participants

4

Reactant 1

HCID 21830659(+/-)-alpha-(6-(Benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanol

Product 1

HCID 21830706alpha-(6-Hydroxy-2-naphthyloxymethyl)-3-pyridinepropanolYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Solid α-(6-(benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanol (0.90 g; from Example 29 above) was dissolved in dry ethanol (20 ml) and hydrogenated for 2 hours at 5 atmospheres pressure using palladium on carbon (10%, 1 spatula end) as catalyst. The reaction was filtered through Celite and the residue washed with ethanol. The combined filtrate and washings were concentrated under reduced pressure and the residue obtained purified by column chromatography over silica eluting with dichloromethane:methanol (95:5) to give a white solid (0.55 g).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washthe residue washed with ethanol
  3. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  4. customthe residue obtained
  5. custompurified by column chromatography over silica eluting with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-1765acf5a7df4f019f4e2394c2bab546
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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