Hydrochloric Acid → HCID 67460460, compound

HRID 554493Notes

Reaction equation

HRID 554493 reaction equation
C([O:8][C:9]1[CH:27]=[CH:26][CH:25]=[CH:24][C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2(O)[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1)C1C=CC=CC=1.Cl.C(=O)([O-])[O-].[K+].[K+]>CO.[OH-].[Pd+2].[OH-]>[CH:18]1([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]=3[OH:8])=[CH:13][CH:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67458564HCID 67458564, compound

Product 1

HCID 67460460HCID 67460460, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[4-(2-benzyloxybenzyl)phenyl]-cyclopentanol (1.14 g, 3.19 mmol) in methanol (21 mL), a 20% palladium hydroxide catalyst (114 mg) was added, and furthermore 36% HCl (0.255 mL) was added thereto. The mixture was stirred under a hydrogen atmosphere overnight, and then cooled to 0° C., potassium carbonate (425 mg) was added thereto and the mixture was stirred for 20 minutes, and then the catalyst was filtered off. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)] to obtain the title compound (744 mg, 92%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. filtrationthe catalyst was filtered off
  3. distillationThe solvent was distilled under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)]

Sources & evidence

ORD record
ord-8969562c17fa49208a590803ddf04639
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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