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

HRID 454012Notes

Reaction equation

HRID 454012 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:32][CH:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]2)(=O)=O)=CC=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:32][CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[CH2:35][CH2:34]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

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

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) was added 4-(4-methylphenylsulphonyloxymethyl)-1-tert-butyloxycarbonylpiperidine (40 g, 0.11 mol). 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 evaporated. 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 (35g, 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. customevaporated
  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-9184d04d7d61489ca6849d08cdb77788
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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