Sodium Carbonate → tert-Butyl 4-(3-phenylisoxazol-5-yl)piperidine-1-carboxylate

HRID 1985475Notes

Reaction equation

HRID 1985475 reaction equation
O[C:2]1([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:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:7]1([C:4]2[CH:3]=[C:2]([CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)[O:6][N:5]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 59731869tert-Butyl 4-(5-hydroxy-3-phenyl-4,5-dihydroisoxazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 59731907tert-Butyl 4-(3-phenylisoxazol-5-yl)piperidine-1-carboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

tert-Butyl 4-(5-hydroxy-3-phenyl-4,5-dihydroisoxazol-5-yl)piperidine-1-carboxylate (320 mg, 0.92 mmol) was dissolved in methanol (10 mL). A solution of sodium carbonate (200 mg, 1.9 mmol) in water (10 mL) was added to the mixture. Reaction was stirred at reflux for 2 hours. Methanol was removed from the reaction mixture in vacuo. Remaining aqueous was extracted 2× ethyl acetate. Combined extracts were washed with brine. Organic layer was dried (magnesium sulfate), filtered, and concentrated. Title compound was obtained as off-white solid in 86% yield. (M−C4H8+H)+=273.1.

Workup

  1. customReaction
  2. temperatureat reflux for 2 hours
  3. customMethanol was removed from the reaction mixture in vacuo
  4. extractionRemaining aqueous was extracted 2× ethyl acetate
  5. washCombined extracts were washed with brine
  6. dry with materialOrganic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d185cab4362e4a42aac01b55390b34c5
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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