3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one → 5-(biphenyl-3-yl)-3-hydroxy-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one

HRID 625972Notes

Reaction equation

HRID 625972 reaction equation
C([O:8][C:9]1[C:10](=[O:37])[N:11]([CH3:36])[C:12]([CH:27]([OH:35])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:17]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=[C:15]([C:13]2[CH:14]=[C:9]([OH:8])[C:10](=[O:37])[N:11]([CH3:36])[C:12]=2[CH:27]([OH:35])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:16]=1

Participants

4

Reactant 1

HCID 711499563-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 533799065-(biphenyl-3-yl)-3-hydroxy-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-oneYield 31.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (100 mg, 0.205 mmol) in 5 mL methanol, was added 10% palladium on charcoal (21.83 mg, 0.02 mmol). The resulting mixture was stirred at room temperature under hydrogen (1 atm) for 45 min. The mixture was filtered to remove charcoal, concentrated and purified by reversed-phase HPLC to afford 5-(biphenyl-3-yl)-3-hydroxy-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (25.4 mg, 0.064 mmol, 31.2% yield). ES-MS (M+H)+=398. High resolution mass spec (ESI) calc (M+H)+=398.1751 found 398.1754

Workup

  1. filtrationThe mixture was filtered
  2. customto remove charcoal
  3. concentrationconcentrated
  4. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-7e548fa82c0640808b5745be5713ce8d
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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