Ammonium Acetate → HCID 58116948, compound

HRID 38539Notes

Reaction equation

HRID 38539 reaction equation
[O:1]1[C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=[N:2]1.O=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[C:7]([C:6]([C:5]1[O:1][N:2]=[CH:3][CH:4]=1)=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)#[N:8]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 49625462-(1,2-Oxazol-5-yl)acetonitrile

Product 1

HCID 58116948HCID 58116948, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of isoxazol-5-ylacetonitrile from Example 48A (3.00 g, 27.8 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (5.53 g, 27.8 mmol) and ammonium acetate (4.28 g, 55.5 mmol) in toluene (50 mL) was heated for 8 h to reflux. Subsequently, the mixture was extracted with water, dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) to yield an oil, which precipitated upon treatment with petroleum ether/tert-butyl methyl ether to yield 4.38 g (54.6%) of the title compound as yellowish crystals.

Workup

  1. temperaturewas heated for 8 h
  2. temperatureto reflux
  3. extractionSubsequently, the mixture was extracted with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)
  7. customto yield an oil, which
  8. customprecipitated upon treatment with petroleum ether/tert-butyl methyl ether

Sources & evidence

ORD record
ord-75460a0c8aa0462ebbccf8d5e3706910
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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