Methanol → HCID 46214870, compound

HRID 880727Notes

Reaction equation

HRID 880727 reaction equation
[C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[C:20]([F:22])[C:19]([O:23]CC4C=CC=CC=4)=[CH:18][C:17]=3[O:31]CC3C=CC=CC=3)[CH2:12][CH2:11]2)=[O:9])C=CC=C[CH:2]=1.CO>C(OCC)(=O)C.[Pd]>[C:16]1([C@@H:1]([NH:7][C:8]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]3[CH:21]=[C:20]([F:22])[C:19]([OH:23])=[CH:18][C:17]=3[OH:31])[CH2:14][CH2:15]2)=[O:9])[CH3:2])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 67423460HCID 67423460, compound

Product 1

HCID 46214870HCID 46214870, compoundYield 144.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 174 mg (0.32 mmol, 1 eq) of 4-(2,4-bis(benzyloxy)-5-fluorophenyl)piperidine-1-carboxylic acid phenylamide in 1 ml of ethyl acetate and of 2 ml of methanol in the presence of 51 mg (30% by mass) of palladium-on-charcoal at 10% is stirred at ambient temperature under atmospheric hydrogen pressure for 8 hours. The reaction medium is filtered through filter paper and the filtrate is evaporated off. The residue is chromatographed on silica gel, elution being carried out with 30/70 heptane/ethyl acetate. 83 mg of 4-(5-fluoro-2,4-dihydroxyphenyl)piperidine-1-carboxylic acid ((S)-1-phenylethyl)amide are obtained.

Workup

  1. filtrationThe reaction medium is filtered
  2. filtrationthrough filter paper
  3. customthe filtrate is evaporated off
  4. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-1f49c6131b1246868821504e8c94a6b0
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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