Methyl 2-(phenoxymethyl)isonicotinate → Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylate

HRID 1963243Notes

Reaction equation

HRID 1963243 reaction equation
[O:1]([CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=1)[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Pt](=O)=O>[CH:2]1([O:1][CH2:8][CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 59536560Methyl 2-(phenoxymethyl)isonicotinate

Product 1

HCID 59536562Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylateYield 73.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 2-(phenoxymethyl)isonicotinate (2.6 g, 10.69 mmol) was dissolved in acetic acid (50 mL), then platinum(IV) oxide (0.243 g, 1.07 mmol) was added and the mixture hydrogenated in a Büchi hydrogenator at 5 bar and room temperature for 6 h. The catalyst was removed by filtration and the solvent evaporated. The residue was taken up in DCM and the organic phase was washed with satd NaHCO3. The aqueous phase was extracted with DCM and the combined organic phases were filtered through a phase separator and evaporated. Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylate (2 g, 73%) was isolated.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. washthe organic phase was washed with satd NaHCO3
  4. extractionThe aqueous phase was extracted with DCM
  5. filtrationthe combined organic phases were filtered through a phase separator
  6. customevaporated

Sources & evidence

ORD record
ord-cf814eaacbf444218c2a998d618227e1
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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