HCID 53696716, compound → HCID 54036729, compound

HRID 1600982Notes

Reaction equation

HRID 1600982 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]([OH:32])[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]([OH:32])[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 53696716HCID 53696716, compound

Product 1

HCID 54036729HCID 54036729, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Solid (2R)-1-(3'-(Benzyloxy)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol (0.88 g, Example 93c) was dissolved in dry ethanol (150 ml) and hydrogenolysed for 24 hours at 3 atmospheres pressure over a palladium on carbon catalyst (10%, 0.09 g). The reaction mixture 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 (98:2) to give the title compound as a white solid (0.52 g).

Workup

  1. filtrationThe reaction mixture 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 (98:2)

Sources & evidence

ORD record
ord-3698c84cfc6142fdb50c148d8d4f1f76
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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