Methanol → 1-Oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid

HRID 1518110ノート

反応式

HRID 1518110 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]([C:11]([O:13]CC)=[O:12])=[N:2]1.CO.O.[OH-].[Li+]>O>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]([C:11]([OH:13])=[O:12])=[N:2]1

参加物

5

反応物 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 59280111Ethyl 1-oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylate

生成物 1

HCID 509941141-Oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid収率 83%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Ethyl 1-oxa-2-aza-spiro[4.5]dec-2-ene-3-carboxylate (8.12 g, 38.5 mmol, as prepared in the previous step) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar, and MeOH (75 mL) and water (25 mL) were added. Lithium hydroxide monohydrate (1.77 g, 42.3 mmol) was added as a solid. The reaction was stirred at RT for 20 h, and the solvents were removed under reduced pressure. The resulting solid was triturated with ether and collected by filtration. The solid was then dissolved in water (200 mL) and acidified to pH 2 with 3 M aq HCl. The precipitate was isolated by filtration, washed well with water, air dried, and dried under vacuum. The filtrate was extracted three times with DCM (50 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The initial precipitate and the material from the extraction were combined, giving 5.81 g (83%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 2.93 (s, 2H), 1.72-1.89 (m, 4H), 1.60-1.72 (m, 2H), 1.37-1.54 (m, 4H).

後処理

  1. customwas placed in a 200 mL round-bottom flask
  2. customequipped with a magnetic stir bar
  3. customthe solvents were removed under reduced pressure
  4. customThe resulting solid was triturated with ether
  5. filtrationcollected by filtration
  6. dissolutionThe solid was then dissolved in water (200 mL)
  7. customThe precipitate was isolated by filtration
  8. washwashed well with water, air
  9. customdried
  10. customdried under vacuum
  11. extractionThe filtrate was extracted three times with DCM (50 mL)
  12. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  13. filtrationfiltered
  14. customthe solvent was removed under reduced pressure
  15. extractionThe initial precipitate and the material from the extraction

出典と根拠

ORDレコード
ord-c5490b4f6a51432185c56e2b8588e245
出典データセット
uspto-grants-2012_07
特許番号
US08232409B2

反応ノート

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