HCID 131722880, compound → (2R, 3RS)-2-(Biphenyl-4-yloxy)-5-pyridin-3-yl-pentan-3-ol

HRID 379963Notes

Reaction equation

HRID 379963 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([O:7][C@@H:8]([CH:10]([OH:19])[C:11]#[C:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH3:9])=[CH:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:2]=[CH:3][C:4]([O:7][C@@H:8]([CH:10]([OH:19])[CH2:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH3:9])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 131722880HCID 131722880, compound

Product 1

HCID 59970467(2R, 3RS)-2-(Biphenyl-4-yloxy)-5-pyridin-3-yl-pentan-3-olYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(2R, 3RS)-2-(Biphenyl-4-yloxy)-5-pyridin-3-yl-pent-4-yn-3-ol (4.86 g, Example 1c) was dissolved in ethyl acetate (100 ml) and hydrogenated at 5 atmospheres using 10% palladium on charcoal (0.5 g) as catalyst. The mixture was filtered through celite® and the filtrate concentrated under reduced pressure to give the title compounds (3.95 g)

Workup

  1. filtrationThe mixture was filtered through celite®
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ba7a203b30f471e9365a7457395479a
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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