Potassium Carbonate → HCID 69320441, compound

HRID 2410364Notes

Reaction equation

HRID 2410364 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([O:11][CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[N:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[O:26]1[C:28]2([CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C.[Cl-].[Na+]>[OH:26][C:28]1([CH2:27][O:1][C:2]2[C:7]3[C:8]([O:11][CH2:12][CH:13]4[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]4)=[N:9][O:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 6379911-Oxaspiro(2.4)heptaneHCID 136263840HCID 136263840, compound

Product 1

HCID 69320441HCID 69320441, compoundYield 74.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 5234Sodium ChlorideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 4-{[(4-hydroxy-1,2-benzisoxazol-3-yl)oxy]methyl}piperidine-1-carboxylate (100 mg, 0.287 mmol, EXAMPLE 17, step 2), 1-oxaspiro[2.4]heptane (59.7 mg, 0.609 mmol), and potassium carbonate (156 mg, 1.13 mmol) in ethanol (2 mL) was heated at 80° C. for 5 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (3 mL) and 5% aq. sodium chloride was added to the mixture. Organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo to give a solid. The residual solid was purified by NH gel column chromatography (ethyl acetate/hexane 1:2) to give 95 mg (74%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionwas added to the mixture
  3. customOrganic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. customThe residual solid was purified by NH gel column chromatography (ethyl acetate/hexane 1:2)

Sources & evidence

ORD record
ord-286b62f8dac24fe995c1f67a89ab3a50
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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