Potassium Carbonate → tert-Butyl 4-((4-(ethoxycarbonyl)-2-methoxyphenoxy)methyl)piperidine-1-carboxylate

HRID 855714Notes

Reaction equation

HRID 855714 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)(=O)=O)=CC=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1O)[C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1[O:11][CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:17][CH2:18]1)[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12038Ethyl vanillateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidine

Product 1

HCID 21874806tert-Butyl 4-((4-(ethoxycarbonyl)-2-methoxyphenoxy)methyl)piperidine-1-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

4-(4-Methylphenylsulphonyloxymethyl)-1-tert-butyloxycarbonylpiperidine (40 g, 0.11 mol) was added to a suspension of ethyl 3-methoxy-4-hydroxybenzoate (19.6 g, 0.1 mol) and potassium carbonate (28 g, 0.2 mol) in dry DMF (200 ml). After stirring at 95° C. for 2.5 hours, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate/ether. The organic layer was washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The resulting oil was crystallised from petroleum ether and the suspension was stored overnight (at 5° C.). The solid was collected by filtration, washed with petroleum ether and dried under vacuum to give ethyl 3-methoxy-4-(1-tert-butyloxycarbonylpiperidin-4-ylmethoxy)benzoate (35 g, 89%).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. custompartitioned between water and ethyl acetate/ether
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles were removed by evaporation
  6. customThe resulting oil was crystallised from petroleum ether
  7. waitthe suspension was stored overnight
  8. custom(at 5° C.)
  9. filtrationThe solid was collected by filtration
  10. washwashed with petroleum ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-c5644f5e5a434a76a949dd9a96d5a027
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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