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

HRID 1693403ノート

反応式

HRID 1693403 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f337735af8c9448fa14e12cef9ccaf60
出典データセット
uspto-grants-2012_04
特許番号
US08158622B2

反応ノート

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