반응 #66817

반응 방정식

isoxazol-5-ylacetonitrile

Isoxazol-5-ylacetonitrile

tert-butyl 4-oxopiperidine-1-carboxylate

ammonium acetate

→

title compound

수율 54.6%

tert-Butyl 4-[cyano(isoxazol-5-yl)methylidene]piperidine-1-carboxylate

수율 54.6%

용매

toluene

반응 조건

후처리

1. 1
   온도was heated for 8 h
2. 2
   온도to reflux
3. 3
   추출Subsequently, the mixture was extracted with water
4. 4
   건조dried over sodium sulfate
5. 5
   기타the solvent was removed in vacuo
6. 6
   기타The crude product was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)
7. 7
   기타to yield an oil, which
8. 8
   기타precipitated upon treatment with petroleum ether/tert-butyl methyl ether

실험 절차

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.

출처