Ethylene Glycol → 1,4-Dioxa-7-azaspiro[4.5]decane

HRID 1693403노트

반응식

HRID 1693403 반응식
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)(OC(C)(C)C)=O.[CH2:15](O)[CH2:16][OH:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[O:14]1[C:10]2([CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[O:17][CH2:16][CH2:15]1

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

생성물 1

HCID 123947731,4-Dioxa-7-azaspiro[4.5]decane

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 1-Boc-3-piperidone (700 mg, 3.51 mmol) in toluene (20 mL) was added ethylene glycol (588 μL, 10.54 mmol) followed by p-toluene sulfonic acid hydrate (1.0 g, 5.27 mmol) and the reaction heated to reflux using Dean-Stark apparatus for 7 h. To the mixture was added NaHCO3 solution, and the organic layer was removed. The aqueous phase was evaporated to dryness and the resulting residue dissolved in THF. Filtration through celite and removal of the solvent in vacuo gave the desired product as light brown oil. δH (CD3OD): 3.99 (2H, s), 3.73-3.57 (2H, m), 3.63 (4H, m), 2.77 (1H, m), 2.73 (1H, m), 1.76 (2H, m).

후처리

  1. temperaturethe reaction heated
  2. temperatureto reflux
  3. customfor 7 h
  4. customthe organic layer was removed
  5. customThe aqueous phase was evaporated to dryness
  6. dissolutionthe resulting residue dissolved in THF
  7. filtrationFiltration
  8. customthrough celite and removal of the solvent in vacuo

출처 및 근거

ORD 기록
ord-f337735af8c9448fa14e12cef9ccaf60
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158622B2

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