Methanol → HCID 67422663, compound

HRID 2365923Notes

Reaction equation

HRID 2365923 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([O:21]CC3C=CC=CC=3)=[CH:16][C:15]=2[O:29]CC2C=CC=CC=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([OH:21])=[CH:16][C:15]=2[OH:29])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 67421015HCID 67421015, compound

Product 1

HCID 67422663HCID 67422663, compoundYield 147.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 860 mg (0.42 mmol, 1 eq) of 4-(2,4-bis(benzyloxy)-5-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester at 35% in 10 ml of ethyl acetate, in the presence of 200 mg of palladium-on-charcoal at 10%, is stirred at ambient temperature under a hydrogen pressure of 5 bar for 17 hours. 5 ml of methanol are added and the reaction medium is stirred at ambient temperature under a hydrogen pressure of 5 bar for 29 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 60/40 heptane/ethyl acetate. 192 mg of 4-(5-fluoro-2,4-dihydroxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester are obtained. Yield=100%.

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-128d363bf84f44e4a9d1ebd55fd6900f
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

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