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

HRID 1767728Notes

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)C=O>[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

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 dimethylformamide (200 ml) and the reaction was heated at 95° C. for 2.5 hours. The reaction was cooled to ambient temperature, partitioned between water and ethyl acetate/diethyl ether, before the organic layer was washed with water and brine. Solvent evaporation in vacuo afforded a clear oil which crystallised on standing. Washing with isohexane and drying in vacuo yielded ethyl 3-methoxy-4-(1-tert-butyloxycarbonylpiperidin-4-ylmethoxy)benzoate (35 g, 89%) as a white solid:

Workup

temperatureThe reaction was cooled to ambient temperature
custompartitioned between water and ethyl acetate/diethyl ether, before the organic layer
washwas washed with water and brine
customSolvent evaporation in vacuo
customafforded a clear oil which
customcrystallised
washWashing with isohexane
customdrying in vacuo

Sources & evidence

ORD record: ord-9bac882f174649e98c6104d4ef4ccd24
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235559B1

Reaction notes

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