HCID 70873408, compound → HCID 70874234, compound

HRID 2172239Notes

Reaction equation

HRID 2172239 reaction equation
C([O:8][CH2:9][CH2:10][C:11]([CH3:40])([OH:39])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[CH3:40][C:11]([OH:39])([CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[CH2:21][CH2:22][CH:23]([CH2:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:34][C:35]([F:38])([F:36])[F:37])=[CH:32][CH:33]=3)[CH2:24][CH2:25]2)=[CH:18][CH:19]=1)[CH2:10][CH2:9][OH:8]

Participants

5

Reactant 2

HCID 70873408HCID 70873408, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70874234HCID 70874234, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

4-Benzyloxy-2-methyl-1-(4-{4-[4-(trifluoromethoxy)phenethyl]piperidin-1-yl}phenoxy)butan-2-ol (2.43 g, 4.5 mmol), ethanol (24 ml) and 20% palladium hydroxide on carbon (0.24 g) were mixed and stirred at 50 to 60° C. under the hydrogen pressure of 1 atm for 4 hours. The mixture was filtered through Celite to remove the catalyst, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100) to afford the title compound as a colorless powder (1.68 g, 80%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100)

Sources & evidence

ORD record
ord-fb4f1ab032124dccb3442d7cd2a9f122
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

Loading…